Ethanol → (4-{[5-Nitro-2-(3-piperidin-1-yl-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester

HRID 1819468노트

반응식

HRID 1819468 반응식
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18](Cl)[N:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[N:34]1([C:40]2[CH:41]=[C:42]([CH:45]=[CH:46][CH:47]=2)[CH2:43][NH2:44])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.CCO>C(Cl)Cl.CC(N(C)C)=O>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:44][CH2:43][C:42]3[CH:45]=[CH:46][CH:47]=[C:40]([N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)[CH:41]=3)[N:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 702EthanolHCID 8471TriethylamineHCID 2795553(3-(1-Piperidyl)phenyl)methanamineHCID 178453940HCID 178453940, 화합물

생성물 1

HCID 57885629(4-{[5-Nitro-2-(3-piperidin-1-yl-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester수율 63%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 31374Dimethylacetamide용매

실험 절차

{trans-4-[(2-Chloro-5-nitro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (200 mg, 0.52 mmol) was dissolved in CH2Cl2 (10 mL) and Et3N (0.289 mL, 2.07 mmol) was added. 3-Piperidin-1-yl-benzylamine (197 mg, 1.04 mmol) was dissolved in DMA:EtOH (2 mL, 1:1) and added to the reaction solution. The reaction was stirred at room temperature for 18 h. The volatiles were removed in vacuo and the crude was purified via flash chromatography (SiO2, 25-50% EtOAc:Hexanes then 5% MeOH:CH2Cl2) to afford 176 mg (63%) of (4-{[5-nitro-2-(3-piperidin-1-yl-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester

후처리

  1. customThe volatiles were removed in vacuo
  2. customthe crude was purified via flash chromatography (SiO2, 25-50% EtOAc

출처 및 근거

ORD 기록
ord-cc85408cc8fa43c4b3e43322edef0a6a
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601714B2

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