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 43975ノート

反応式

HRID 43975 の反応式
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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7519Anisole溶媒

反応条件

温度
45 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0b4693a0466b433bacb635cee146a4db
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

反応ノート

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