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

HRID 1819468Notes

Reaction equation

HRID 1819468 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

{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

Workup

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

Sources & evidence

ORD record
ord-cc85408cc8fa43c4b3e43322edef0a6a
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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