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

HRID 1878346Notes

Reaction equation

HRID 1878346 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]([Cl:30])[CH:3]=1.Cl[C:32](OC1C=CC([N+]([O-])=O)=CC=1)=[O:33].[CH2:44]([NH2:48])[CH:45]([CH3:47])[CH3:46]>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:32]([NH:48][CH2:44][CH:45]([CH3:47])[CH3:46])=[O:33])=[CH:3][C:4]=3[Cl:30])[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 6558IsobutylamineHCID 821294-Nitrophenyl chloroformateHCID 579176443-((4-(4-Amino-2-chlorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Product 1

HCID 57917671N-tert-Butyl-3-((4-(2-chloro-4-(3-isobutylureido)benzoyl)piperazin-1-yl)methyl)benzamideYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-2-chlorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (250 mg, 0.625 mmol) and 4-nitrophenol chloroformate (126 mg, 0.625 mmol) were combined and stirred in dichloromethane for 1 hour. Isobutylamine (87.8 mg, 1.2 mol, 0.12 mL) was added and the reaction was stirred for 30 minutes. The reaction mixture was diluted with water and flushed through a hydrophobic frit. The reaction was concentrated under reduced pressure to give a residue, which was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 4% methanol/dichloromethane) to afford the title compound (178.1 mg).

Workup

  1. customflushed through a hydrophobic frit
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customto give a residue, which
  4. customwas purified by silica chromatography (
  5. washeluting with a solvent gradient from dichloromethane to 4% methanol/dichloromethane)

Sources & evidence

ORD record
ord-ac62e7bbfb394a7498014a3392c90864
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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