CN103896941A - Synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-formonitrile - Google Patents
Synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-formonitrile Download PDFInfo
- Publication number
- CN103896941A CN103896941A CN201410131661.8A CN201410131661A CN103896941A CN 103896941 A CN103896941 A CN 103896941A CN 201410131661 A CN201410131661 A CN 201410131661A CN 103896941 A CN103896941 A CN 103896941A
- Authority
- CN
- China
- Prior art keywords
- pyridine
- chloropyridine
- formonitrile hcn
- synthetic method
- ethyl acetate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- PZIUWGQZDDJQMW-UHFFFAOYSA-N 6-chloroimidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1=C(Cl)C=CC2=NC=C(C#N)N21 PZIUWGQZDDJQMW-UHFFFAOYSA-N 0.000 title abstract 5
- 238000001308 synthesis method Methods 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 53
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 17
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000003810 ethyl acetate extraction Methods 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 90
- 239000000460 chlorine Substances 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 238000010189 synthetic method Methods 0.000 claims description 18
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000001953 recrystallisation Methods 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- DREUPRFRJOSEAM-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1=CC=CN2C(C#N)=CN=C21 DREUPRFRJOSEAM-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- NRADUXZAWBQICJ-IZZDOVSWSA-N ClC=1C=CC(=NC1)/N=C/N(C)C Chemical compound ClC=1C=CC(=NC1)/N=C/N(C)C NRADUXZAWBQICJ-IZZDOVSWSA-N 0.000 abstract 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 20
- REPVNSJSTLRQEQ-UHFFFAOYSA-N n,n-dimethylacetamide;n,n-dimethylformamide Chemical compound CN(C)C=O.CN(C)C(C)=O REPVNSJSTLRQEQ-UHFFFAOYSA-N 0.000 description 17
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 15
- 238000000967 suction filtration Methods 0.000 description 12
- 238000000605 extraction Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- -1 extraction Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to a synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-formonitrile. The synthesis method of the 6-chloroimidazo[1,2-a]pyridine-3-formonitrile comprises the following steps: reacting 2-amino-5-chloropyridine and N,N-dimethylformamide dimethylacetal at a temperature ranging from 50 to 110 DEG C for 2-10 hours to obtain (E)-N'-(5-chloropyridine-2-yl)-N,N-dimethylformamidine, next, reacting (E)-N'-(5-chloropyridine-2-yl)-N,N-dimethylformamidine with bromoacetonitrile at a temperature ranging from 50 to 150 DEG C for 5-35 hours under the action of a base in a solvent, then carrying out ethyl acetate extraction, water washing, drying and rotary evaporation and concentration to obtain the coarse product of the 6-chloroimidazo[1,2-a]pyridine-3-formonitrile, and recrystallizing the coarse product solvent to obtain the pure product. The synthesis method of the 6-chloroimidazo[1,2-a]pyridine-3-formonitrile has the beneficial effects of mild reaction conditions, easiness for operation, stable product quality and high product purity.
Description
(1) technical field
The invention belongs to organic synthesis field, be specifically related to the synthetic method of a kind of 6-chlorine imidazo [1,2-a] pyridine-3-formonitrile HCN.
(2) background technology
The chloro-imidazo of 6-[1,2-a] pyridine-3-formonitrile HCN is a kind of important pharmaceutical intermediate, the chloro-imidazo [1 of existing 6-, 2-a] in pyridine-3-formonitrile HCN preparation process, reaction is fierce, complex operation, in product, foreign matter content is high, and output is only 40% left and right, and the problems referred to above need to improve.
(3) summary of the invention
The present invention, in order to make up the deficiencies in the prior art, provides a kind of 6-chlorine imidazo [1,2-a] pyridine-3-synthetic method of formonitrile HCN, and this synthetic method is simple to operate, productive rate is high, is applicable to laboratory and suitability for industrialized production.
The present invention is achieved through the following technical solutions:
A kind of synthetic method of 6-chlorine imidazo [1,2-a] pyridine-3-formonitrile HCN, its special character is: comprise the following steps:
(1) preparation (E)-N'-(5-chloropyridine-2-yl)-N, N-dimethyl carbonamidine: 2-amino-5-chloropyridine and N, dinethylformamide dimethylacetal (being called for short DMF-DMA) makes (E)-N'-(5-chloropyridine-2-yl)-N, N-dimethyl carbonamidine for 2-10 hour 50-110 DEG C of reaction;
(2) preparing product: in solvent, (E)-N'-(5-chloropyridine-2-yl)-N, N-dimethyl carbonamidine reacts 5-35 hour in 50-150 DEG C with bromoacetonitrile under alkali effect, then after ethyl acetate extraction, water washing, dry, rotary evaporation are concentrated 6-chlorine imidazo [1,2-a] the thick product of pyridine-3-formonitrile HCN, after thick product solvent recrystallization, obtain sterling.
The synthetic method of 6-chlorine imidazo of the present invention [1,2-a] pyridine-3-formonitrile HCN, in step (1), 2-amino-5-chloropyridine: N, weight ratio=the 1:2.8-3.5 of dinethylformamide dimethylacetal, in step (2), 2-amino-5-chloropyridine: the weight ratio of solvent is 1:5.9-7.3.
The synthetic method of 6-chlorine imidazo of the present invention [1,2-a] pyridine-3-formonitrile HCN, in step (2), solvent is DMF (being called for short DMF), tetrahydrofuran (THF), acetonitrile or N, any one material in N-dimethyl acetyl ammonia (being called for short DMA).
The synthetic method of 6-chlorine imidazo of the present invention [1,2-a] pyridine-3-formonitrile HCN, in step (2), raw material consumption is: 2-amino-5-chloropyridine: bromoacetonitrile: the mol ratio of alkali is 1:1.5-2.0:1.5-2.0.
The synthetic method of 6-chlorine imidazo of the present invention [1,2-a] pyridine-3-formonitrile HCN, in step (2), alkali is the one in sodium bicarbonate, triethylamine, sodium hydroxide and saleratus.
The synthetic method of 6-chlorine imidazo of the present invention [1,2-a] pyridine-3-formonitrile HCN, in step (2), recrystallization solvent is respectively dehydrated alcohol and ethyl acetate/normal hexane mixed solvent, wherein ethyl acetate: the volume ratio of normal hexane is 1:2.
The synthetic method of 6-chlorine imidazo of the present invention [1,2-a] pyridine-3-formonitrile HCN, in step (2), uses anhydrous sodium sulfate drying.
Beneficial effect of the present invention: adopt the present invention to prepare 6-chlorine imidazo [1,2-a] pyridine-3-formonitrile HCN, reaction conditions gentleness, easy handling, and constant product quality, purity is high.
(4) embodiment
Embodiment 1:
In 50mL single necked round bottom flask, add 2-amino-5-chloropyridine (3.86g, 30mmol) and DMF-DMA(12mL), heated and stirred reaction, temperature of reaction is 100-110 DEG C, after 4h, reaction finishes; Rotary evaporation is removed DMF-DMA, is transferred in 100mL flask, does not need further processing, directly adds 30mLDMF, 3.78g sodium bicarbonate and the reaction of 5.40g bromoacetonitrile heated and stirred, and temperature of reaction is 130-140 DEG C, finishes reaction after 15h.Reaction mixture is transferred in large beaker, adds 200mL ethyl acetate, suction filtration, and filter residue fully washs by ethyl acetate; In filtrate, add 150mL water, extraction, 200mL ethyl acetate extraction for water, merges organic phase, adds anhydrous sodium sulphate fully dry.After suction filtration, rotary evaporation is removed ethyl acetate and is obtained brown solid, and this obtains 3.85g faint yellow solid, productive rate 72.2%, fusing point 180.2-183.0 DEG C after dehydrated alcohol, ethyl acetate/normal hexane 1:2 solution difference recrystallization for brown solid.
Embodiment 2:
In 50mL single necked round bottom flask, add 2-amino-5-chloropyridine (3.86g, 30mmol) and DMF-DMA(15mL), heated and stirred reaction, temperature of reaction is 50-55 DEG C, after 3h, reaction finishes; Rotary evaporation is removed DMF-DMA, is transferred in 100mL flask, does not need further processing, directly adds 30mLDMA, 5.10g saleratus and the reaction of 6.12g bromoacetonitrile heated and stirred, and temperature of reaction is 50-55 DEG C, finishes reaction after 18h.Reaction mixture is transferred in large beaker, adds 200mL ethyl acetate, suction filtration, and filter residue fully washs by ethyl acetate; In filtrate, add 150mL water, extraction, 200mL ethyl acetate extraction for water, merges organic phase, adds anhydrous sodium sulphate fully dry.After suction filtration, rotary evaporation is removed ethyl acetate and is obtained brown solid, and this obtains 3.60g faint yellow solid, productive rate 67.5%, fusing point 180.5-183.0 DEG C after dehydrated alcohol, ethyl acetate/normal hexane 1:2 solution difference recrystallization for brown solid.
Embodiment 3:
In 250mL single necked round bottom flask, add 2-amino-5-chloropyridine (38.6g, 300mmol) and DMF-DMA(120mL), heated and stirred reaction, temperature of reaction is 100-110 DEG C, after 4h, reaction finishes; Rotary evaporation is removed DMF-DMA, does not need further processing, directly adds 250mLDMF, 37.8g sodium bicarbonate and the reaction of 54.0g bromoacetonitrile heated and stirred, and temperature of reaction is 105-110 DEG C, finishes reaction after 16h.Reaction mixture is transferred in large beaker, adds 400mL ethyl acetate, suction filtration, and filter residue fully washs by ethyl acetate; In filtrate, add 300mL water, extraction, ethyl acetate for water (2 × 300mL) extraction, merges organic phase, adds anhydrous sodium sulphate fully dry.After suction filtration, rotary evaporation is removed ethyl acetate and is obtained brown solid, and this obtains 35.6g faint yellow solid, productive rate 66.8%, 180.0～183.5 DEG C of fusing points after dehydrated alcohol, ethyl acetate/normal hexane 1:2 solution difference recrystallization for brown solid.
Embodiment 4:
In 250mL single necked round bottom flask, add 2-amino-5-chloropyridine (38.6g, 300mmol) and DMF-DMA(120mL), heated and stirred reaction, temperature of reaction is 70-80 DEG C, after 4h, reaction finishes; Rotary evaporation is removed DMF-DMA, does not need further processing, directly adds 250mLDMA, 51.0g saleratus and the reaction of 61.2g bromoacetonitrile heated and stirred, and temperature of reaction is 75-85 DEG C, finishes reaction after 20h.Reaction mixture is transferred in large beaker, adds 400mL ethyl acetate, suction filtration, and filter residue fully washs by ethyl acetate; In filtrate, add 300mL water, extraction, ethyl acetate for water (2 × 300mL) extraction, merges organic phase, adds anhydrous sodium sulphate fully dry.After suction filtration, rotary evaporation is removed ethyl acetate and is obtained brown solid, and this obtains 33.8g faint yellow solid, productive rate 63.4%, 179.8～183.0 DEG C of fusing points after dehydrated alcohol, ethyl acetate/normal hexane 1:2 solution difference recrystallization for brown solid.
Embodiment 5:
In 250mL single necked round bottom flask, add 2-amino-5-chloropyridine (38.6g, 300mmol) and DMF-DMA(120mL), heated and stirred reaction, temperature of reaction is 90-100 DEG C, after 3.5h, reaction finishes; Rotary evaporation is removed DMF-DMA, does not need further processing, directly adds 300mL tetrahydrofuran (THF), 20.4g sodium hydroxide and the reaction of 61.2g bromoacetonitrile heated and stirred, and temperature of reaction is 60-65 DEG C, finishes reaction after 25h.Reaction mixture is transferred in large beaker, adds 400mL ethyl acetate, suction filtration, and filter residue fully washs by ethyl acetate; In filtrate, add 300mL water, extraction, ethyl acetate for water (2 × 300mL) extraction, merges organic phase, adds anhydrous sodium sulphate fully dry.After suction filtration, rotary evaporation is removed ethyl acetate and is obtained brown solid, and this obtains 30.8g faint yellow solid, productive rate 57.8%, fusing point 179.5-182.0 DEG C after dehydrated alcohol, ethyl acetate/normal hexane 1:2 solution difference recrystallization for brown solid.
Embodiment 6:
In 250mL single necked round bottom flask, add 2-amino-5-chloropyridine (38.6g, 300mmol) and DMF-DMA(120mL), heated and stirred reaction, temperature of reaction is 105-110 DEG C, after 3.5h, reaction finishes; Rotary evaporation is removed DMF-DMA, does not need further processing, directly adds 300mL acetonitrile, 48.6g triethylamine and the reaction of 57.6g bromoacetonitrile heated and stirred, and temperature of reaction is 70-80 DEG C, finishes reaction after 25h.Reaction mixture is transferred in large beaker, adds 400mL ethyl acetate, suction filtration, and filter residue fully washs by ethyl acetate; In filtrate, add 300mL water, extraction, ethyl acetate for water (2 × 300mL) extraction, merges organic phase, adds anhydrous sodium sulphate fully dry.After suction filtration, rotary evaporation is removed ethyl acetate and is obtained brown solid, and this obtains 25.6g faint yellow solid, productive rate 48.0%, 179.5～182.2 DEG C of fusing points after dehydrated alcohol, ethyl acetate/normal hexane 1:2 solution difference recrystallization for brown solid.
Embodiment 7:
Add DMF-DMA(13mL), heated and stirred reaction, temperature of reaction is 105-110 DEG C, after 2h, reaction finishes; Rotary evaporation is removed DMF-DMA, do not need further processing, directly add 24mLDMF, 5.04g sodium bicarbonate and the reaction of 7.2g bromoacetonitrile heated and stirred, temperature of reaction is 150 DEG C, after 5h, finish reaction, after recrystallization, obtain 3.72g faint yellow solid, productive rate 69.8%, 180.2～183.0 DEG C of fusing points, other are identical with embodiment 1.
Embodiment 8:
Add DMF-DMA(14mL), heated and stirred reaction, temperature of reaction is 100-105 DEG C, after 10h, reaction finishes; Rotary evaporation is removed DMF-DMA, do not need further processing, directly add 25mLDMF, 3.78g sodium bicarbonate and the reaction of 5.40g bromoacetonitrile heated and stirred, temperature of reaction is 145 DEG C, after 35h, finish reaction, after recrystallization, obtain 3.74g faint yellow solid, productive rate 70.2%, 180～183 DEG C of fusing points, other are identical with embodiment 1.
Claims (7)
1. the synthetic method of a 6-chlorine imidazo [1,2-a] pyridine-3-formonitrile HCN, is characterized in that: comprise the following steps:
(1) preparation (E)-N'-(5-chloropyridine-2-yl)-N, N-dimethyl carbonamidine: 2-amino-5-chloropyridine and N, dinethylformamide dimethylacetal makes (E)-N'-(5-chloropyridine-2-yl)-N, N-dimethyl carbonamidine for 2-10 hour 50-110 DEG C of reaction;
(2) preparing product: in solvent, (E)-N'-(5-chloropyridine-2-yl)-N, N-dimethyl carbonamidine reacts 5-35 hour in 50-150 DEG C with bromoacetonitrile under alkali effect, then after ethyl acetate extraction, water washing, dry, rotary evaporation are concentrated 6-chlorine imidazo [1,2-a] the thick product of pyridine-3-formonitrile HCN, after thick product solvent recrystallization, obtain sterling.
2. 6-chlorine imidazo [1 according to claim 1,2-a] synthetic method of pyridine-3-formonitrile HCN, it is characterized in that: in step (1), 2-amino-5-chloropyridine: N, weight ratio=the 1:2.8-3.5 of dinethylformamide dimethylacetal, in step (2), 2-amino-5-chloropyridine: the weight ratio of solvent is 1:5.9-7.3.
3. 6-chlorine imidazo [1 according to claim 1 and 2,2-a] synthetic method of pyridine-3-formonitrile HCN, it is characterized in that: in step (2), solvent is N, dinethylformamide, tetrahydrofuran (THF), acetonitrile or N, any one material in N-dimethyl acetyl ammonia.
4. the synthetic method of 6-chlorine imidazo according to claim 1 and 2 [1,2-a] pyridine-3-formonitrile HCN, is characterized in that: in step (2), raw material consumption is: 2-amino-5-chloropyridine: bromoacetonitrile: the mol ratio of alkali is 1:1.5-2.0:1.5-2.0.
5. the synthetic method of 6-chlorine imidazo according to claim 1 and 2 [1,2-a] pyridine-3-formonitrile HCN, is characterized in that: in step (2), alkali is the one in sodium bicarbonate, triethylamine, sodium hydroxide and saleratus.
6. 6-chlorine imidazo [1 according to claim 1 and 2,2-a] synthetic method of pyridine-3-formonitrile HCN, it is characterized in that: in step (2), recrystallization solvent is respectively dehydrated alcohol and ethyl acetate/normal hexane mixed solvent, wherein ethyl acetate: the volume ratio of normal hexane is 1:2.
7. the synthetic method of 6-chlorine imidazo according to claim 1 and 2 [1,2-a] pyridine-3-formonitrile HCN, is characterized in that: in step (2), use anhydrous sodium sulfate drying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410131661.8A CN103896941A (en) | 2014-04-03 | 2014-04-03 | Synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-formonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410131661.8A CN103896941A (en) | 2014-04-03 | 2014-04-03 | Synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-formonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103896941A true CN103896941A (en) | 2014-07-02 |
Family
ID=50988559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410131661.8A Pending CN103896941A (en) | 2014-04-03 | 2014-04-03 | Synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-formonitrile |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103896941A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650079A (en) * | 2015-01-31 | 2015-05-27 | 山东友帮生化科技有限公司 | Synthesis method of 8-methoxylimidazo[1,2a]pyridine-3-carbonitrile |
| CN104829617A (en) * | 2015-04-25 | 2015-08-12 | 山东友帮生化科技有限公司 | Synthesis method for 6-fluoroimidazo[1, 2-a]pyridine-3-carbonitrile |
| CN104910151A (en) * | 2015-05-29 | 2015-09-16 | 山东友帮生化科技有限公司 | 6-phenyl-8-acetonitrile oxy imidazo [1,2-a] pyridine-3-carbonitrile preparation method |
| CN107778200A (en) * | 2016-08-24 | 2018-03-09 | 广东东阳光药业有限公司 | The method for preparing Amitraz |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012034091A1 (en) * | 2010-09-09 | 2012-03-15 | Irm Llc | Imidazo [1, 2] pyridazin compounds and compositions as trk inhibitors |
| CN103130792A (en) * | 2011-11-30 | 2013-06-05 | 江苏正大天晴药业股份有限公司 | 2-aminothiazoles compound |
-
2014
- 2014-04-03 CN CN201410131661.8A patent/CN103896941A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012034091A1 (en) * | 2010-09-09 | 2012-03-15 | Irm Llc | Imidazo [1, 2] pyridazin compounds and compositions as trk inhibitors |
| CN103130792A (en) * | 2011-11-30 | 2013-06-05 | 江苏正大天晴药业股份有限公司 | 2-aminothiazoles compound |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650079A (en) * | 2015-01-31 | 2015-05-27 | 山东友帮生化科技有限公司 | Synthesis method of 8-methoxylimidazo[1,2a]pyridine-3-carbonitrile |
| CN104829617A (en) * | 2015-04-25 | 2015-08-12 | 山东友帮生化科技有限公司 | Synthesis method for 6-fluoroimidazo[1, 2-a]pyridine-3-carbonitrile |
| CN104910151A (en) * | 2015-05-29 | 2015-09-16 | 山东友帮生化科技有限公司 | 6-phenyl-8-acetonitrile oxy imidazo [1,2-a] pyridine-3-carbonitrile preparation method |
| CN107778200A (en) * | 2016-08-24 | 2018-03-09 | 广东东阳光药业有限公司 | The method for preparing Amitraz |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103896941A (en) | Synthesis method of 6-chloroimidazo[1,2-a]pyridine-3-formonitrile | |
| CN102863408B (en) | Preparation method of andrographolide | |
| CN101475539B (en) | Refining method for preparing high-purity oteracil potassium | |
| CN103965191A (en) | Synthesis method of 6-bromoimidazo[1,2-alpha]pyridyl-3-formic acid | |
| CN103360412A (en) | A kind of synthetic method of S 578 | |
| CN105585539A (en) | One-pot ceftazidime side-chain acid ethyl ester synthesis method | |
| CN104086463B (en) | The preparation method of a kind of Isosorbide-5-Nitrae-Ding disulfonic acid fine work and solution thereof | |
| CN104844525A (en) | Preparation method of rosuvastatin calcium impurity | |
| CN104478974B (en) | A kind of 20, the synthetic method of 23-dipiperidino-5-O-mycamino syl-tylono lide | |
| CN103880843A (en) | Method for synthetizing 6-bromine imidazo [1, 2-alpha] pyridine-3-carbonitrile | |
| CN104402881B (en) | A kind of synthetic method of 3-aldehyde radical-6-bromine imidazo [1,2-a] pyridine-8-ethyl formate | |
| CN104402882A (en) | Synthetic method of ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate | |
| CN103709174A (en) | One-step synthesis method of 6-bromo-3H-oxazolo [4,5-b] pyridine-2-ketone | |
| CN103965192B (en) | A kind of synthetic method of 6-chlorine imidazo [1,2-a] Nicotinicum Acidum | |
| CN104844598A (en) | Synthesis method of 8-methoxy ethyl formate imidazole and [1,2a]pyridine-3-ethyl formate | |
| CN104910153A (en) | 6-chloro-8-acetonitrile oxy imidazo [1,2-a] pyridine-3-carbonitrile preparation method | |
| CN105646472A (en) | Preparation method of arotinolol hydrochloride | |
| CN103833751B (en) | The synthesis technique of a kind of vinpocetin related impurities A | |
| CN104529847A (en) | Method for producing methomyl | |
| CN102977104A (en) | Synthesis of 2,4-dichloro-7-hydroxy-pyrrolo(2,3)pyrimidine | |
| CN103288822A (en) | Preparation method of vinpocetine | |
| CN104557922A (en) | Synthetic method for 6-bromoimidazo[1,2-a]pyridine-8-carboxylic acid | |
| CN106632355A (en) | Synthesis method of 6-bromoimidazo[1,2-b]pyridazine | |
| CN102391079B (en) | Method for preparing chiral biphenyl cyclooctadiene lignan compound | |
| CN102276576B (en) | Benzamide compound and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20140702 |