Pyrazole → 3-(1-{[2-(1H-pyrazol-1-yl)-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

HRID 383781

반응식

HRID 383781 반응식
Br[C:2]1[CH:7]=[C:6]([C:8]([N:10]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1.[NH:35]1[CH:39]=[CH:38][CH:37]=[N:36]1.C(=NO)C1C(=CC=CC=1)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.[Cu-]=O>[N:35]1([C:2]2[CH:7]=[C:6]([C:8]([N:10]3[CH2:14][CH2:13][CH:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH2:11]3)=[O:9])[CH:5]=[CH:4][C:3]=2[C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[CH:39]=[CH:38][CH:37]=[N:36]1

참가 물질

7

반응물 4

HCID 1048PyrazoleHCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 866577533-(1-{[2-Bromo-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

생성물 1

HCID 468475913-(1-{[2-(1H-pyrazol-1-yl)-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

A solution of 3b (54.0 mg, 0.099 mmol), pyrazole (50.7 mg, 0.745 mmol), salicylaldoxime (19.8 mg, 0.145 mmol), copper(I) oxide (16.6 mg, 0.116 mmol) and cesium carbonate (265 mg, 0.812 mmol) in acetonitrile (1.00 mL) was heated to 120° C. in a sealed microwave vial for a total of 60 min. The reaction mixture was cooled to rt, concentrated in vacuo, and the resulting crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 10a. m/z (ES) 531 (MH)+.

후처리

  1. concentrationconcentrated in vacuo
  2. customthe resulting crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)

출처 및 근거

ORD 기록
ord-a453bc123ad646129051bb5ef7295e14
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367679B2

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