Piperidine-1-propylamine → N-(2-t-butoxycarbonylaminophenyl)-4-{2-[(3-piperidin-1-ylpropyl)amino]pyrimidin-4-yl}benzamide

HRID 888028

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][N:36]=[C:35](Cl)[N:34]=2)=[CH:29][CH:28]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C)C(=O)C>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([NH:1][CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[N:34]=2)=[CH:29][CH:28]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 24 mm×150 mm pyrex tube, charged with 3-aminopropylpiperidine (73 mg, 0.51 mmol), was added a solution of N-(2-t-butoxycarbonylaminophenyl)-4-(2-chloropyrimidin-4-yl)benzamide (Method 52, 85 mg, 0.20 mmol) in N,N-dimethylacetamide (4.6 ml). The reaction mixture was then heated to 50° C. and stirred for 16 hours, before being evaporated to dryness. The resultant residue was purified by flash chromatography, on silica (10 g), eluting with methanol/dichloromethane (5-15%), to give the title compound (48 mg, 45%); Mass Spectrum: M+H+ 531.

Workup

custombefore being evaporated to dryness
customThe resultant residue was purified by flash chromatography, on silica (10 g)
washeluting with methanol/dichloromethane (5-15%)

Sources & evidence

ORD record: ord-9eed615c0eff4748a94176f0642fa04c
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247562B2

Linked notes

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