1-Methylpiperazine → N-(2-t-Butoxycarbonylaminophenyl)-4-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]benzamide

HRID 888038Notes

Reaction equation

HRID 888038 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:30])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][N:26]=[C:25](Cl)[N:24]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:30])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([N:35]3[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]3)[N:24]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 86599911N-(2-t-butoxycarbonylaminophenyl)-4-(2-chloropyrimidin-4-yl)benzamide

Product 1

HCID 68407682N-(2-t-Butoxycarbonylaminophenyl)-4-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]benzamideYield 71%

Procedure

Using an analogous procedure to that described in Method 41, the N-(2-t-butoxycarbonylaminophenyl)-4-(2-chloropyrimidin-4-yl)benzamide (Method 52, 59 mg, 0.14 mmol) was reacted with 1-methylpiperazine (77 mg, 0.69 mmol) and residue purified by flash chromatography eluting with methanol/dichloromethane (0-20%) to give the title compound (48 mg, 71%); Mass Spectrum: M+H+ 489.

Workup

  1. custompurified by flash chromatography
  2. washeluting with methanol/dichloromethane (0-20%)

Sources & evidence

ORD record
ord-2b1a4689e04240b2acd658ef4e235f90
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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