Cyclobutylamine → N-tert-Butyl-3-((4-(4-(3-cyclobutylureido)-2,5-difluorobenzoyl)piperazin-1-yl)methyl)-benzamide

HRID 1878349Notes

Reaction equation

HRID 1878349 reaction equation
[NH2:1][C:2]1[C:29]([F: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]([F:31])[CH:3]=1.Cl[C:33](OC1C=CC([N+]([O-])=O)=CC=1)=[O:34].[CH:45]1([NH2:49])[CH2:48][CH2:47][CH2:46]1>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]([F:30])[C:2]([NH:1][C:33]([NH:49][CH:45]4[CH2:48][CH2:47][CH2:46]4)=[O:34])=[CH:3][C:4]=3[F:31])[CH2:13][CH2:12]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 75645CyclobutylamineHCID 821294-Nitrophenyl chloroformateHCID 57917587HCID 57917587, compound

Product 1

HCID 57917656N-tert-Butyl-3-((4-(4-(3-cyclobutylureido)-2,5-difluorobenzoyl)piperazin-1-yl)methyl)-benzamideYield 2.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-2,5-difluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (1 g, 0.023 mol) and 4-nitrophenol chloroformate (0.4636 g, 0.0023 mol) were combined and stirred in dichloromethane for 1 hour at room temperature. Cyclobutylamine (0.8969 g, 0.0017 mol, 0.108 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 organic phase was concentrated under vacuum and purified by acidic reverse phase HPLC to afford the title compound (21 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-47f323ff7d404814a03c9ed506a6ca5c
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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