Trifluoroacetic acid → cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide

HRID 43975노트

반응식

HRID 43975 반응식
ClC1N=C(C(N[C@H]2CCN(C3N=NN(CC4C=CC(OC)=CC=4)N=3)C[C@H]2OC)=O)NC=1CC.[Cl:34][C:35]1[N:36]=[C:37]([C:42]([NH:44][C@H:45]2[CH2:50][CH2:49][N:48]([C:51]([C:53]3[N:54]=[N:55][NH:56][N:57]=3)=[O:52])[CH2:47][C@H:46]2[O:58][CH3:59])=[O:43])[NH:38][C:39]=1[CH2:40][CH3:41].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[Cl:34][C:35]1[N:36]=[C:37]([C:42]([NH:44][C@H:45]2[CH2:50][CH2:49][N:48]([C:51]([C:53]3[N:54]=[N:55][NH:56][N:57]=3)=[O:52])[CH2:47][C@H:46]2[O:58][CH3:59])=[O:43])[NH:38][C:39]=1[CH2:40][CH3:41]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86762084cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(4-methoxybenzyl)-2H-tetrazol-5-yl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide

생성물 1

HCID 86762083cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide수율 21.4%

시약·촉매·용매 1

HCID 7519Anisole용매

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온도
45 °C

실험 절차

cis(±)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide cis(±)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(4-methoxybenzyl)-2H-tetrazol-5-yl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide obtained in Example (260a) (28 mg, 0.05 mmol) was dissolved in anisole (1 mL). Trifluoroacetic acid (2 mL) was added, and the mixture was stirred at 45° C. for 3.5 hours. Following concentration under reduced pressure, the reaction solution was diluted and extracted with dichloromethane and aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was solidified by adding chloroform and hexane to obtain 4.1 mg of the title compound as a white solid (20%).

후처리

  1. concentrationconcentration under reduced pressure
  2. additionthe reaction solution was diluted
  3. extractionextracted with dichloromethane and aqueous sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionby adding chloroform and hexane

출처 및 근거

ORD 기록
ord-0b4693a0466b433bacb635cee146a4db
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536197B2

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