CN104610164B - 2‑(2‑正丁基‑4‑羟基‑6‑甲基‑嘧啶‑5‑基)‑n,n‑二甲基乙酰胺的制备方法 - Google Patents
2‑(2‑正丁基‑4‑羟基‑6‑甲基‑嘧啶‑5‑基)‑n,n‑二甲基乙酰胺的制备方法 Download PDFInfo
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- CN104610164B CN104610164B CN201410817307.0A CN201410817307A CN104610164B CN 104610164 B CN104610164 B CN 104610164B CN 201410817307 A CN201410817307 A CN 201410817307A CN 104610164 B CN104610164 B CN 104610164B
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- formula
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- 238000002360 preparation method Methods 0.000 title claims description 27
- LVILGAOSPDLNRM-UHFFFAOYSA-N 4-methylpyrimidine Chemical compound CC1=CC=NC=N1 LVILGAOSPDLNRM-UHFFFAOYSA-N 0.000 title 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical class CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 23
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 11
- 239000005475 Fimasartan Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229960003489 fimasartan Drugs 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- AMEROGPZOLAFBN-UHFFFAOYSA-N fimasartan Chemical compound CCCCC1=NC(C)=C(CC(=S)N(C)C)C(=O)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 AMEROGPZOLAFBN-UHFFFAOYSA-N 0.000 claims description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- -1 Methyl Chemical group 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 3
- YWOITFUKFOYODT-UHFFFAOYSA-N methanol;sodium Chemical compound [Na].OC YWOITFUKFOYODT-UHFFFAOYSA-N 0.000 claims 1
- 229960004448 pentamidine Drugs 0.000 abstract description 6
- OAMDXZTUOHORAO-UHFFFAOYSA-N 2-(2-butyl-6-methyl-4-oxo-1h-pyrimidin-5-yl)-n,n-dimethylacetamide Chemical compound CCCCC1=NC(=O)C(CC(=O)N(C)C)=C(C)N1 OAMDXZTUOHORAO-UHFFFAOYSA-N 0.000 abstract description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- FFHQVTXPIOPINO-UHFFFAOYSA-N pentanimidamide;hydrochloride Chemical compound Cl.CCCCC(N)=N FFHQVTXPIOPINO-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 2
- BATGDOSJDGVCBF-UHFFFAOYSA-N C(CC(=O)C)(=O)OCCCC(=O)N(C)C Chemical compound C(CC(=O)C)(=O)OCCCC(=O)N(C)C BATGDOSJDGVCBF-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- XREKLQOUFWBSFH-UHFFFAOYSA-N dimethyl 2-acetylbutanedioate Chemical compound COC(=O)CC(C(C)=O)C(=O)OC XREKLQOUFWBSFH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
- 102000008873 Angiotensin II receptor Human genes 0.000 description 1
- 108050000824 Angiotensin II receptor Proteins 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- DZOSHZFEUHWZKB-UHFFFAOYSA-N methyl 2-acetyl-4-(dimethylamino)-4-oxobutanoate Chemical compound COC(=O)C(C(C)=O)CC(=O)N(C)C DZOSHZFEUHWZKB-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000003087 receptor blocking agent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2010-0005725 | 2010-01-21 | ||
| KR20100005725 | 2010-01-21 | ||
| KR20100005945A KR101058284B1 (ko) | 2010-01-22 | 2010-01-22 | 2-(2-ｎ-부틸-4-히드록시-6-메틸-피리미딘-5-일)-Ｎ,Ｎ-디메틸아세트아미드의 신규한 제조방법 |
| KR10-2010-0005945 | 2010-01-22 | ||
| CN201180004629.8A CN102666496B (zh) | 2010-01-21 | 2011-01-20 | 2-(2-正丁基-4-羟基-6-甲基-嘧啶-5-基)-n,n-二甲基乙酰胺的制备方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180004629.8A Division CN102666496B (zh) | 2010-01-21 | 2011-01-20 | 2-(2-正丁基-4-羟基-6-甲基-嘧啶-5-基)-n,n-二甲基乙酰胺的制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104610164A CN104610164A (zh) | 2015-05-13 |
| CN104610164B true CN104610164B (zh) | 2018-03-16 |
Family
ID=44307398
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410817307.0A Expired - Fee Related CN104610164B (zh) | 2010-01-21 | 2011-01-20 | 2‑(2‑正丁基‑4‑羟基‑6‑甲基‑嘧啶‑5‑基)‑n,n‑二甲基乙酰胺的制备方法 |
| CN201180004629.8A Expired - Fee Related CN102666496B (zh) | 2010-01-21 | 2011-01-20 | 2-(2-正丁基-4-羟基-6-甲基-嘧啶-5-基)-n,n-二甲基乙酰胺的制备方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180004629.8A Expired - Fee Related CN102666496B (zh) | 2010-01-21 | 2011-01-20 | 2-(2-正丁基-4-羟基-6-甲基-嘧啶-5-基)-n,n-二甲基乙酰胺的制备方法 |
Country Status (3)
| Country | Link |
|---|---|
| CN (2) | CN104610164B (cg-RX-API-DMAC7.html) |
| IN (1) | IN2012DN02695A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011090323A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140096514A (ko) * | 2013-01-28 | 2014-08-06 | 보령제약 주식회사 | 암 예방 또는 치료용 조성물 |
| CN110123771A (zh) | 2013-03-14 | 2019-08-16 | 保宁制药株式会社 | 药物组合药物 |
| CN104478811B (zh) * | 2014-11-14 | 2017-01-25 | 浙江浙邦制药有限公司 | 一种非马沙坦中间体的制备方法 |
| CN107973784B (zh) * | 2017-11-16 | 2021-08-24 | 珠海市海瑞德生物科技有限公司 | 一种非马沙坦的合成方法 |
| CN113121484A (zh) * | 2019-12-31 | 2021-07-16 | 复星弘创(苏州)医药科技有限公司 | 一种制备3-位被酰胺基烷基取代的香豆素类化合物的方法及其产物和相关中间体 |
| CN113336709B (zh) * | 2021-06-25 | 2022-06-03 | 上海立科化学科技有限公司 | 一种n,n-二甲基乙酰胺的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999055681A1 (en) * | 1998-04-25 | 1999-11-04 | Boryung Pharmaceutical Co., Ltd. | Pyrimidinone compounds, pharmaceutical compositions containing the compounds and the process for preparing the same |
| CN1558906A (zh) * | 2001-09-21 | 2004-12-29 | 保宁制药株式会社 | 嘧啶酮化合物及其药学上可接受的盐的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100521980B1 (ko) * | 2002-10-10 | 2005-10-17 | 보령제약 주식회사 | 피리미디논 화합물 및 이의 염의 삼수화물의 제조 방법 |
-
2011
- 2011-01-20 WO PCT/KR2011/000401 patent/WO2011090323A2/en not_active Ceased
- 2011-01-20 IN IN2695DEN2012 patent/IN2012DN02695A/en unknown
- 2011-01-20 CN CN201410817307.0A patent/CN104610164B/zh not_active Expired - Fee Related
- 2011-01-20 CN CN201180004629.8A patent/CN102666496B/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999055681A1 (en) * | 1998-04-25 | 1999-11-04 | Boryung Pharmaceutical Co., Ltd. | Pyrimidinone compounds, pharmaceutical compositions containing the compounds and the process for preparing the same |
| CN1558906A (zh) * | 2001-09-21 | 2004-12-29 | 保宁制药株式会社 | 嘧啶酮化合物及其药学上可接受的盐的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011090323A2 (en) | 2011-07-28 |
| CN102666496B (zh) | 2015-05-20 |
| WO2011090323A3 (en) | 2011-11-10 |
| IN2012DN02695A (cg-RX-API-DMAC7.html) | 2015-09-04 |
| CN104610164A (zh) | 2015-05-13 |
| CN102666496A (zh) | 2012-09-12 |
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Granted publication date: 20180316 |