Isobutylamine → N-tert-Butyl-3-((4-(5-chloro-4-(3-isobutylureido)-2-methoxybenzoyl)piperazin-1-yl)methyl)-benzamide

HRID 1878351Notes

Reaction equation

HRID 1878351 reaction equation
[NH2:1][C:2]1[C:29]([Cl:30])=[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:31][CH3:32])[CH:3]=1.Cl[C:34](OC1C=CC([N+]([O-])=O)=CC=1)=[O:35].[CH2:46]([NH2:50])[CH:47]([CH3:49])[CH3:48]>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[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]3[CH:28]=[C:29]([Cl:30])[C:2]([NH:1][C:34]([NH:50][CH2:46][CH:47]([CH3:49])[CH3:48])=[O:35])=[CH:3][C:4]=3[O:31][CH3:32])[CH2:13][CH2:12]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 6558IsobutylamineHCID 821294-Nitrophenyl chloroformateHCID 579175773-((4-(4-amino-5-chloro-2-methoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Product 1

HCID 57917623N-tert-Butyl-3-((4-(5-chloro-4-(3-isobutylureido)-2-methoxybenzoyl)piperazin-1-yl)methyl)-benzamideYield 1.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-5-chloro-2-methoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (1.712 g, 0.0037 mol) and 4-nitrophenol chloroformate (0.7518 g, 0.0037 mol) were combined and stirred at room temperature in dichloromethane for 1 hour. Isobutylamine (0.1536 g 0.208 mol) was added and the reaction was stirred for a further 30 minutes. The reaction mixture was diluted with water and flushed through a hydrophobic frit. The organic phase was concentrated under vacuum and purified by acidic reverse phase HPLC affording the title compound (37 mg).

Workup

  1. customflushed through a hydrophobic frit
  2. concentrationThe organic phase was concentrated under vacuum
  3. custompurified by acidic reverse phase HPLC

Sources & evidence

ORD record
ord-9eaea7fdda9d436ca12eb3950abdc3a7
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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