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 643724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643724
[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]

Komponenten

5

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fc468ba1f1604f4e88de3ab5fc388fe4
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700624B2

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