Cyclobutylamine → N-tert-Butyl-5-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)furan-2-carboxamide

HRID 408857Notes

Reaction equation

HRID 408857 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[O:19][C:18]([C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:29].Cl[C:31](OC1C=CC([N+]([O-])=O)=CC=1)=[O:32].[CH:43]1([NH2:47])[CH2:46][CH2:45][CH2:44]1>ClCCl.O>[C:23]([NH:22][C:20]([C:18]1[O:19][C:15]([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]3[CH:27]=[CH:28][C:2]([NH:1][C:31]([NH:47][CH:43]4[CH2:46][CH2:45][CH2:44]4)=[O:32])=[C:3]([F:29])[CH:4]=3)[CH2:13][CH2:12]2)=[CH:16][CH:17]=1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 75645CyclobutylamineHCID 821294-Nitrophenyl chloroformateHCID 666615235-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylfuran-2-carboxamide

Product 1

HCID 44634489N-tert-Butyl-5-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)furan-2-carboxamideYield 8.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylfuran-2-carboxamide (113 mg, 0.280 mmol) and 4-nitrophenol chloroformate (56 mg, 0.238 mmol) were combined and stirred in dichloromethane for 1 hour at room temperature. Cyclobutylamine (59.6 mg, 0.839 mmol, 71.6 μl) 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 (10 mg). MS (ESI) m/z 500.3 [M+H]+

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-bbe1515fb112457b91a886d0fc3b9d10
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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