CN112759592A - Synthetic method of 6-iodo [1,2,3] triazolo [1,5-a ] pyridine - Google Patents
Synthetic method of 6-iodo [1,2,3] triazolo [1,5-a ] pyridine Download PDFInfo
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- JVQZQGRMJKRVIP-UHFFFAOYSA-N IC=1C=CC=2N(C=1)N=NC=2 Chemical compound IC=1C=CC=2N(C=1)N=NC=2 JVQZQGRMJKRVIP-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000010189 synthetic method Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000001914 filtration Methods 0.000 claims abstract description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000000706 filtrate Substances 0.000 claims abstract description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000005406 washing Methods 0.000 claims abstract description 16
- 239000012043 crude product Substances 0.000 claims abstract description 15
- 239000012074 organic phase Substances 0.000 claims abstract description 15
- 239000000047 product Substances 0.000 claims abstract description 15
- 238000003756 stirring Methods 0.000 claims abstract description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000012065 filter cake Substances 0.000 claims abstract description 8
- 239000012452 mother liquor Substances 0.000 claims abstract description 8
- 150000002923 oximes Chemical class 0.000 claims abstract description 8
- 238000004537 pulping Methods 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 238000004321 preservation Methods 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 239000008399 tap water Substances 0.000 claims description 7
- 235000020679 tap water Nutrition 0.000 claims description 7
- 238000005057 refrigeration Methods 0.000 claims description 5
- 238000002474 experimental method Methods 0.000 abstract description 2
- 230000035484 reaction time Effects 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 229910052723 transition metal Inorganic materials 0.000 abstract description 2
- 150000003624 transition metals Chemical class 0.000 abstract description 2
- 239000012266 salt solution Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 controlling T <10 °C Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
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Classifications
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
A method for synthesizing 6-iodo [1,2,3] triazolo [1,5-a ] pyridine comprises the following steps: adding 800g of 600-800g of oxime and 3-4L of anhydrous tetrahydrofuran into a 10L reaction bottle, stirring, filtering, recovering toluene from the filter cake by 2L x 3 for pulping, sequentially extracting mother liquor of the first filtration from the filtrate for three times, combining organic phase 2L saturated salt solution for washing, concentrating under reduced pressure to dryness to obtain 750-800g crude product of 7.5-8L methanol and 70-85g activated carbon, refluxing for 1h, filtering while hot, washing filter residue with 0.5L hot methanol, concentrating the filtrate under reduced pressure to about 4L, refrigerating in a refrigerator, filtering to obtain the product without transition metal, and has the advantages of high and rapid reaction, mild conditions, simple and easily obtained substrate, wide applicability, short reaction time, high yield and the like, meanwhile, the post-treatment of the reaction is simple and convenient, the harm to experiment operators is reduced, the environment is friendly, and the requirements of green chemistry are met.
Description
Technical Field
The invention relates to the technical field of pyridine synthesis, in particular to a synthesis method of 6-iodo [1,2,3] triazolo [1,5-a ] pyridine.
Background
In recent years, coordination chemistry has been remarkably developed in the chemical field, and a large number of complexes having novel structures are designed and synthesized by coordinating organic polydentate ligands containing nitrogen, phosphorus, oxygen, and the like with different metals. Among them, pyridine derivatives, which are one of the most widely used ligands, have been a focus of coordination chemistry because of their strong coordination ability, diverse coordination modes, and the ability to form a complex compound with stable structure with various metal ions.
The pyridine derivative ligand can synthesize various complexes with novel structures and excellent properties through the actions of coordination bonds, hydrogen bonds, pi-pi stacking on aromatic rings and the like, and the metal organic complex has more reaction sites and higher catalytic activity, so the metal organic complex is widely used for a series of organic synthesis reactions such as coupling reaction, hydrogen transfer reaction, esterification reaction, olefin double decomposition reaction, olefin polymerization reaction, oxidation reaction, hydrogenation reaction and the like. In addition, the complex has good application prospects in the aspects of gas storage, ion exchange, molecular recognition, chiral resolution, hydrogen storage, drug slow release and the like. Therefore, the design and synthesis of the pyridine derivative ligand are of great significance to the research field and the catalytic industry field.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a synthetic method of 6-iodo [1,2,3] triazolo [1,5-a ] pyridine.
(II) technical scheme
In order to achieve the purpose, the invention provides the following technical scheme: a method for synthesizing 6-iodo [1,2,3] triazolo [1,5-a ] pyridine comprises the following steps:
step 1, putting 800g of 600-plus-one oxime and 3-4L of anhydrous tetrahydrofuran into a 10L reaction bottle, stirring, replacing nitrogen in vacuum, cooling to 0 ℃, dropwise adding 700g of trifluoroacetic anhydride, controlling T <10 ℃, completing the addition, naturally heating to room temperature, releasing heat, heating to about 40 ℃, cooling tap water, performing heat preservation reaction for 3 hours at about 30 ℃, detecting no raw material by TLC, then cooling to 0 ℃, dropwise adding a solution of 700-plus-one 800g of sodium carbonate/3L of water, controlling T <10 ℃, stirring for 0.5 hour at room temperature, and filtering;
step 2, recovering toluene from the filter cake by using 2L x 3, pulping, sequentially extracting the mother liquor of the first filtration from the filtrate for three times, combining organic phases, washing with 2L saturated saline solution, and concentrating under reduced pressure until the organic phases are dried to obtain 800g of crude products of 750-;
and 3, adding 7.5-8L of methanol and 70-85g of activated carbon into the crude product, refluxing for 1h, filtering while the product is hot, washing filter residues with 0.5L of hot methanol, concentrating the filtrate under reduced pressure to about 4L, refrigerating in a freezer, and filtering to obtain the product.
As an improvement of the invention, the method comprises the following steps:
step 1, putting 780g of oxime and 4L of anhydrous tetrahydrofuran into a 10L reaction bottle, stirring, performing vacuum nitrogen replacement, cooling to 0 ℃, dropwise adding 685g of trifluoroacetic anhydride, controlling T <10 ℃, naturally heating to room temperature, releasing heat, heating to about 40 ℃, cooling tap water, performing heat preservation reaction for 3 hours at about 30 ℃, detecting no raw material by TLC, cooling to 0 ℃, dropwise adding 780g of sodium carbonate/3L of water solution, controlling T <10 ℃, stirring for 0.5 hour at room temperature after adding, and filtering;
step 2, recovering toluene from the filter cake by using 2L x 3, pulping, sequentially extracting the mother liquor of the first filtration from the filtrate for three times, combining organic phases, washing with 2L saturated saline solution, and concentrating under reduced pressure until the organic phases are dried to obtain 770g of crude products;
and 3, adding 7.8L of methanol and 78g of activated carbon into the crude product, refluxing for 1h, filtering while the product is hot, washing filter residues by using 0.5L of hot methanol, concentrating the filtrate under reduced pressure to about 4L, putting the filtrate into a freezer for refrigeration, and filtering to obtain the product.
The hot filtration in step 3 is preheated in an oven using a buchner funnel as a modification of the invention.
(III) advantageous effects
Compared with the prior art, the invention provides a synthesis method of 6-iodo [1,2,3] triazolo [1,5-a ] pyridine, which has the following beneficial effects:
the new method is simple in reaction operation, can synthesize the 6-iodo [1,2,3] triazolo [1,5-a ] pyridine by simple steps, is realized under the condition of no transition metal, has the advantages of high efficiency and rapidness in reaction, mild condition, simple and easily obtained substrate, wide applicability, short reaction time, high yield and the like, is simple and convenient in post-treatment of the reaction, reduces the harm to experiment operators, is environment-friendly, and meets the requirement of green chemistry.
Drawings
FIG. 1 is a reaction scheme of the present invention;
FIG. 2 is a chart of hydrogen carbon of the compound of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A method for synthesizing 6-iodo [1,2,3] triazolo [1,5-a ] pyridine comprises the following steps:
step 1, putting 600g of oxime and 3L of anhydrous tetrahydrofuran into a 10L reaction bottle, stirring, performing vacuum nitrogen replacement, cooling to 0 ℃, dropwise adding 650g of trifluoroacetic anhydride, controlling T <10 ℃, finishing addition, naturally heating to room temperature, releasing heat, heating to about 40 ℃, cooling tap water, performing heat preservation reaction at about 30 ℃ for 3 hours, detecting no raw material by TLC, cooling to 0 ℃, dropwise adding 700g of sodium carbonate/3L of water solution, controlling T <10 ℃, finishing the addition, stirring at the room temperature for 0.5 hours, and filtering;
step 2, recovering toluene from the filter cake by using 2L x 3, pulping, sequentially extracting the mother liquor of the first filtration from the filtrate for three times, combining organic phases, washing with 2L saturated saline solution, and concentrating under reduced pressure until the organic phases are dried to obtain 750g of crude products;
and 3, adding 7.5L of methanol and 70g of activated carbon into the crude product, refluxing for 1h, filtering while the product is hot, washing filter residues by using 0.5L of hot methanol, concentrating the filtrate under reduced pressure to about 4L, putting the filtrate into a freezer for refrigeration, and filtering to obtain the product.
Example 2
Step 1, putting 780g of oxime and 4L of anhydrous tetrahydrofuran into a 10L reaction bottle, stirring, performing vacuum nitrogen replacement, cooling to 0 ℃, dropwise adding 685g of trifluoroacetic anhydride, controlling T <10 ℃, naturally heating to room temperature, releasing heat, heating to about 40 ℃, cooling tap water, performing heat preservation reaction for 3 hours at about 30 ℃, detecting no raw material by TLC, cooling to 0 ℃, dropwise adding 780g of sodium carbonate/3L of water solution, controlling T <10 ℃, stirring for 0.5 hour at room temperature after adding, and filtering;
step 2, recovering toluene from the filter cake by using 2L x 3, pulping, sequentially extracting the mother liquor of the first filtration from the filtrate for three times, combining organic phases, washing with 2L saturated saline solution, and concentrating under reduced pressure until the organic phases are dried to obtain 770g of crude products;
and 3, adding 7.8L of methanol and 78g of activated carbon into the crude product, refluxing for 1h, filtering while the product is hot, washing filter residues by using 0.5L of hot methanol, concentrating the filtrate under reduced pressure to about 4L, putting the filtrate into a freezer for refrigeration, and filtering to obtain the product.
Example 3
A method for synthesizing 6-iodo [1,2,3] triazolo [1,5-a ] pyridine comprises the following steps:
step 1, putting 800g of oxime and 4L of anhydrous tetrahydrofuran into a 10L reaction bottle, stirring, performing vacuum nitrogen replacement, cooling to 0 ℃, dropwise adding 700g of trifluoroacetic anhydride, controlling T to be less than 10 ℃, finishing addition, naturally heating to room temperature, releasing heat, heating to about 40 ℃, cooling tap water, performing heat preservation reaction at about 30 ℃ for 3 hours, detecting no raw material by TLC, cooling to 0 ℃, dropwise adding a solution of 800g of sodium carbonate/3L of water, controlling T to be less than 10 ℃, finishing addition, stirring at room temperature for 0.5 hours, and filtering;
step 2, recovering toluene from the filter cake by using 2L x 3, pulping, sequentially extracting the mother liquor of the first filtration from the filtrate for three times, combining organic phases, washing with 2L saturated saline solution, and concentrating under reduced pressure until the organic phases are dried to obtain 800g of crude products;
and 3, adding 8L of methanol and 85g of activated carbon into the crude product, refluxing for 1h, filtering while the product is hot, washing filter residue by using 0.5L of hot methanol, concentrating the filtrate under reduced pressure to about 4L, putting the filtrate into a freezer for refrigeration, and filtering to obtain the product.
In three examples, step 3 was filtered while hot using a buchner funnel and preheated in an oven as a modification of the invention.
(HPLC conditions: MeOH: 0.1% TFA ═ 70:30,254nm)
The boiling point of the toluene is higher, the vacuum degree required by the reduced pressure concentration is higher, the water solubility of the ethyl acetate is larger, the ethyl acetate is not easy to separate from water, and the required amount is much larger than that of the toluene. The actual production can be selected according to the conditions.
The metering in specific example 2 can be referred to the following table
| Material(s) | Molecular weight | Weight (D) | Number of moles | Molar ratio of |
| Oxime compounds | 263.04 | 780g | 2.963 | 1.00 |
| Trifluoroacetic anhydride | 210.03 | 685g | 3.261 | 1.10 |
| Tetrahydrofuran (THF) | 4.0L | |||
| Sodium carbonate | 106.00 | 780g | 2.48 | |
| Activated carbon | 78g | |||
| Sodium chloride | 500g | |||
| Methanol | 8.3L | |||
| Toluene | 6L | |||
| Cyclic compound | 245.02 | 439g |
Molar yield: 60.4 percent
Weight yield: 56.3 percent
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (3)
1. A method for synthesizing 6-iodo [1,2,3] triazolo [1,5-a ] pyridine is characterized by comprising the following steps:
step 1, putting 800g of 600-plus-one oxime and 3-4L of anhydrous tetrahydrofuran into a 10L reaction bottle, stirring, replacing nitrogen in vacuum, cooling to 0 ℃, dropwise adding 700g of trifluoroacetic anhydride, controlling T <10 ℃, completing the addition, naturally heating to room temperature, releasing heat, heating to about 40 ℃, cooling tap water, performing heat preservation reaction for 3 hours at about 30 ℃, detecting no raw material by TLC, then cooling to 0 ℃, dropwise adding a solution of 700-plus-one 800g of sodium carbonate/3L of water, controlling T <10 ℃, stirring for 0.5 hour at room temperature, and filtering;
step 2, recovering toluene from the filter cake by using 2L x 3, pulping, sequentially extracting the mother liquor of the first filtration from the filtrate for three times, combining organic phases, washing with 2L saturated saline solution, and concentrating under reduced pressure until the organic phases are dried to obtain 800g of crude products of 750-;
and 3, adding 7.5-8L of methanol and 70-85g of activated carbon into the crude product, refluxing for 1h, filtering while the product is hot, washing filter residues with 0.5L of hot methanol, concentrating the filtrate under reduced pressure to about 4L, refrigerating in a freezer, and filtering to obtain the product.
2. The method of synthesizing 6-iodo [1,2,3] triazolo [1,5-a ] pyridine according to claim 1, comprising the steps of:
step 1, putting 780g of oxime and 4L of anhydrous tetrahydrofuran into a 10L reaction bottle, stirring, performing vacuum nitrogen replacement, cooling to 0 ℃, dropwise adding 685g of trifluoroacetic anhydride, controlling T <10 ℃, naturally heating to room temperature, releasing heat, heating to about 40 ℃, cooling tap water, performing heat preservation reaction for 3 hours at about 30 ℃, detecting no raw material by TLC, cooling to 0 ℃, dropwise adding 780g of sodium carbonate/3L of water solution, controlling T <10 ℃, stirring for 0.5 hour at room temperature after adding, and filtering;
step 2, recovering toluene from the filter cake by using 2L x 3, pulping, sequentially extracting the mother liquor of the first filtration from the filtrate for three times, combining organic phases, washing with 2L saturated saline solution, and concentrating under reduced pressure until the organic phases are dried to obtain 770g of crude products;
and 3, adding 7.8L of methanol and 78g of activated carbon into the crude product, refluxing for 1h, filtering while the product is hot, washing filter residues by using 0.5L of hot methanol, concentrating the filtrate under reduced pressure to about 4L, putting the filtrate into a freezer for refrigeration, and filtering to obtain the product.
3. The method for synthesizing 6-iodo [1,2,3] triazolo [1,5-a ] pyridine according to claim 2, wherein the hot filtration in step 3 is preheated in an oven by using a Buchner funnel.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1658866A (en) * | 2002-04-04 | 2005-08-24 | 比奥根艾迪克Ma公司 | Tri-substituted heteroaryls and methods of making and using the same |
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| CN103764655A (en) * | 2011-07-13 | 2014-04-30 | Sk化学公司 | 2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| CN111479809A (en) * | 2017-12-13 | 2020-07-31 | 劲方医药科技(上海)有限公司 | Crystal form and salt form of TGF- β RI inhibitor and preparation method thereof |
-
2021
- 2021-02-01 CN CN202110138097.2A patent/CN112759592A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1658866A (en) * | 2002-04-04 | 2005-08-24 | 比奥根艾迪克Ma公司 | Tri-substituted heteroaryls and methods of making and using the same |
| CN1770980A (en) * | 2003-02-12 | 2006-05-10 | 比奥根艾迪克Ma公司 | Pyrazoles and methods of making and using the same |
| CN103764655A (en) * | 2011-07-13 | 2014-04-30 | Sk化学公司 | 2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| CN111479809A (en) * | 2017-12-13 | 2020-07-31 | 劲方医药科技(上海)有限公司 | Crystal form and salt form of TGF- β RI inhibitor and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 樊红莉: "6-取代［1,2,4］三唑并［1,5-a］吡啶的合成", 《化学试剂》 * |
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