Cyclohexanemethylamine → HCID 178511538, compound

HRID 1819377Notes

Reaction equation

HRID 1819377 reaction equation
C(OC(=O)[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](Cl)[N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.[CH:27]1([CH2:33][NH2:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:34][CH2:33][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[N:17]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 76688CyclohexanemethylamineHCID 57885529(4-[(2-Chloro-5-nitro-pyrimidin-4-ylamino)-methyl]cyclohexyl)-carbamic acid tert-butyl ester

Product 1

HCID 178511538HCID 178511538, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above {4-[(2-chloro-5-nitro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (50.2 mg, 0.13 mmol) in CH2Cl2 (0.8 mL) was added cyclohexylmethylamine (44.1 mg, 0.39 mmol). The reaction mixture was stirred at room temperature for 3 h and then purified by silica gel column chromatography using 50:1 CH2Cl2;MeOH as an eluent to afford 32 mg (54%) of the desired product as a pale yellow solid.

Workup

  1. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-d6626290a27546f0b3c02281dce80060
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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