Isobutylamine → N-tert-Butyl-3-((4-(4-(3-isobutylureido)-2-methoxybenzoyl)piperazin-1-yl)methyl)benzamide

HRID 1878353Notes

Reaction equation

HRID 1878353 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=3)[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]2)=[O:7])=[C:4]([O:30][CH3:31])[CH:3]=1.Cl[C:33](OC1C=CC([N+]([O-])=O)=CC=1)=[O:34].[CH2:45]([NH2:49])[CH:46]([CH3:48])[CH3:47]>ClCCl.O>[C:21]([NH:20][C:18](=[O:19])[C:17]1[CH:25]=[CH:26][CH:27]=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]3[CH:28]=[CH:29][C:2]([NH:1][C:33]([NH:49][CH2:45][CH:46]([CH3:48])[CH3:47])=[O:34])=[CH:3][C:4]=3[O:30][CH3:31])[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 6558IsobutylamineHCID 821294-Nitrophenyl chloroformateHCID 579176893-((4-(4-Amino-2-methoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Product 1

HCID 57917622N-tert-Butyl-3-((4-(4-(3-isobutylureido)-2-methoxybenzoyl)piperazin-1-yl)methyl)benzamideYield 26.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-2-methoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (200 mg, 0.48 mmol) and 4-nitrophenol chloroformate (475 mg, 0.48 mmol) were combined and stirred in dichloromethane for 1 hour. Isobutylamine (102.4 mg, 1.4 mmol, 0.14 mL) was added and the reaction mixture was stirred for 30 minutes. The reaction mixture was diluted with water and flushed through a hydrophobic fret. The organic phase was concentrated under reduced pressure and purified by acidic reverse phase HPLC to afford the title compound (67 mg). MS (ESI) m/z 524.5 [M+H]+

Workup

  1. customflushed through
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. custompurified by acidic reverse phase HPLC

Sources & evidence

ORD record
ord-7440fccbd83e49979c468c811d416021
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

Loading…