Acetic Acid → 4-[3-(4-Hydroxy-4-phenyl-piperidin-1-yl)-propyl]-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one

HRID 1096236노트

반응식

HRID 1096236 반응식
[O:1]=[C:2]1[N:8]([CH2:9][CH2:10][CH:11]=O)[CH2:7][CH2:6][N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:4][CH2:3]1.[C:23]1([C:29]2([OH:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.B.N1C=CC=CC=1.CC(O)=O>ClCCCl.CCO>[OH:35][C:29]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:34][CH2:33][N:32]([CH2:11][CH2:10][CH2:9][N:8]2[C:2](=[O:1])[CH2:3][CH2:4][N:5]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH2:6][CH2:7]2)[CH2:31][CH2:30]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 963874-Phenylpiperidin-4-olHCID 2723995Borane;pyridineHCID 866383883-[7-Oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-propionaldehyde

생성물 1

HCID 591592464-[3-(4-Hydroxy-4-phenyl-piperidin-1-yl)-propyl]-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one수율 44%

시약·촉매·용매 1

HCID 229016121,2-Dichloroethane ethanol용매

실험 절차

To a solution of 3-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-propionaldehyde 0.016 g (0.05 mmol) and 4-phenyl-piperidin-4-ol 0.018 g (0.10 mmol) in DCE/EtOH 1:1 (0.5 ml) was added pyridine-borane complex (25 μL of 8 M solution in pyridine, 0.2 mmol) and AcOH (25 μL, 0.4 mmol) and the mixture stirred for 16 h. The mixture was then evaporated to dryness and purified by preparative HPLC, affording the title compound 0.01 g (44%) as a white solid. MS: 476.2 (MH+).

후처리

  1. customThe mixture was then evaporated to dryness
  2. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-08bf37eec1154abcab77aabfd51a5773
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138175B2

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