Sodium triacetoxyborohydride → 4-{[(1R,3S)-3-isopropyl-3-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl)carbonyl)cyclopentyl]amino}-1-(5-pyrimidin-2-ylpyridin-2-yl}cyclohexanol

HRID 643724ノート

反応式

HRID 643724 の反応式
[NH2:1][C@@H:2]1[CH2:6][CH2:5][C@@:4]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])([CH:7]([CH3:9])[CH3:8])[CH2:3]1.[OH:28][C:29]1([C:36]2[CH:41]=[CH:40][C:39]([C:42]3[N:47]=[CH:46][CH:45]=[CH:44][N:43]=3)=[CH:38][N:37]=2)[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:7]([C@:4]1([C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=3)[CH2:16][CH2:17]2)=[O:11])[CH2:5][CH2:6][C@@H:2]([NH:1][CH:32]2[CH2:31][CH2:30][C:29]([C:36]3[CH:41]=[CH:40][C:39]([C:42]4[N:43]=[CH:44][CH:45]=[CH:46][N:47]=4)=[CH:38][N:37]=3)([OH:28])[CH2:34][CH2:33]2)[CH2:3]1)([CH3:8])[CH3:9]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 578033584-Hydroxy-4-[5-(2-pyrimidinyl)-2-pyridyl]cyclohexanoneHCID 57938734((1S,3R)-3-amino-1-isopropylcyclopentyl)(4-(4-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)methanone

生成物 1

HCID 236302124-{[(1R,3S)-3-isopropyl-3-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl)carbonyl)cyclopentyl]amino}-1-(5-pyrimidin-2-ylpyridin-2-yl}cyclohexanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of ((1S,3R)-3-amino-1-isopropylcyclopentyl)(4-(4-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)methanone (50 mg, 0.13 mmol) in DCM (2 mL) was added 4-hydroxy-4-(5-(pyrimidin-2-yl)pyridin-2-yl)cyclohexanone (1.5 equiv) and sodium triacetoxyborohydride (1.5 equiv). The mixture was stirred until complete, portioned and the aqueous phase extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate. Chromatography gave the title compound as a white powder after lypholization. MS calculated for C32H42F3N7O2: (M+H) 638; found 638.3.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate

出典と根拠

ORDレコード
ord-fc468ba1f1604f4e88de3ab5fc388fe4
出典データセット
uspto-grants-2010_04
特許番号
US07700624B2

反応ノート

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