Water → 4-(5-{3-[5-(1-Methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-ureido}-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1993687노트

반응식

HRID 1993687 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(Cl)(Cl)C[O:24][C:25](=O)[NH:26][C:27]1[N:28]([C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=2)[N:29]=[C:30]([C:32]2([CH3:35])[CH2:34][CH2:33]2)[CH:31]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:25]([NH:26][C:27]3[N:28]([C:36]4[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=4)[N:29]=[C:30]([C:32]4([CH3:35])[CH2:33][CH2:34]4)[CH:31]=3)=[O:24])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 17999304tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylateHCID 57832815[5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloroethyl ester

생성물 1

HCID 591344584-(5-{3-[5-(1-Methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-ureido}-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Heat a solution of 4-(5-amino-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (Preparation 4, 1.05 equiv, 0.5845 g), [5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloroethyl ester (Preparation 39, 1.0 equiv, 0.8054 g) and diisopropylethylamine (2 equiv, 0.7 mL) in DMSO (0.25 M, 8 mL) to 60° C. for 6 hours. Cool the resulting mixture to ambient temperature, and add water (20 mL). Extract with EtOAc (2×25 mL), then wash the combined organic phases with water (10 mL) and saturated aq. sodium chloride solution (10 mL). Dry over MgSO4, then subject residue to silica gel chromatography eluting with a gradient 2 M ammonia-methanol in dichloromethane. LCMS(ES+): m/z=532.3 [M+H].

후처리

  1. extractionExtract with EtOAc (2×25 mL)
  2. washwash the combined organic phases with water (10 mL) and saturated aq. sodium chloride solution (10 mL)
  3. dry with materialDry over MgSO4
  4. washsubject residue to silica gel chromatography eluting with a gradient 2 M ammonia-methanol in dichloromethane

출처 및 근거

ORD 기록
ord-f6648675a0e84196bc684251fb0bf8bb
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652015B2

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