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 643724Notes

Reaction equation

HRID 643724 reaction equation
[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]

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-fc468ba1f1604f4e88de3ab5fc388fe4
Source dataset
uspto-grants-2010_04
Patent number
US07700624B2

Reaction notes

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