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

HRID 1878355Notes

Reaction equation

HRID 1878355 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])=[CH:4][C:3]=1[O:30][C:31]([F:34])([F:33])[F:32].Cl[C:36](OC1C=CC([N+]([O-])=O)=CC=1)=[O:37].[CH2:48]([NH2:52])[CH:49]([CH3:51])[CH3:50]>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]=[CH:29][C:2]([NH:1][C:36]([NH:52][CH2:48][CH:49]([CH3:51])[CH3:50])=[O:37])=[C:3]([O:30][C:31]([F:33])([F:34])[F:32])[CH:4]=3)[CH2:13][CH2:12]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 6558IsobutylamineHCID 821294-Nitrophenyl chloroformateHCID 579176403-((4-(4-Amino-3-(trifluoromethoxy)benzoyl)piperazin-1-yl)methyl)-N-tert-butyl-benzamide

Product 1

HCID 57917708N-tert-Butyl-3-((4-(4-(3-isobutylureido)-3-(trifluoromethoxy)benzoyl)piperazin-1-yl)methyl)benzamideYield 6.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-3-(trifluoromethoxy)benzoyl)piperazin-1-yl)methyl)—N-tert-butyl-benzamide (250 mg, 0.525 mmol) and 4-nitrophenol chloroformate (106 mg, 0.525 mmol) were combined and stirred in dichloromethane for 1 hour. Isobutylamine (0.115 g, 1.6 mmol, 0.156 mL) was added and the reaction mixture 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 basic reverse phase HPLC to afford the title compound (20 mg), MS (ESI) m/z 578.5 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-d5581edbbf114add8b051329fc29c95d
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

Loading…