2-Fluorophenyl isocyanate → N-tert-Butyl-3-((4-(3-fluoro-4-(3-(2-fluorophenyl)ureido)benzoyl)piperazin-1-yl)methyl)benzamide

HRID 1878334Notes

Reaction equation

HRID 1878334 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[F:30].[F:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]=[C:39]=[O:40]>ClCCl>[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:39]([NH:38][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[F:31])=[O:40])=[C:3]([F:30])[CH:4]=3)[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 855882-Fluorophenyl isocyanateHCID 668785283-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Product 1

HCID 57917627N-tert-Butyl-3-((4-(3-fluoro-4-(3-(2-fluorophenyl)ureido)benzoyl)piperazin-1-yl)methyl)benzamideYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (100 mg, 0.242 mmol) and 2-fluorophenylisocyanate (37 mg, 0.267 mmol) were combined and heated in dichloromethane at 100° C. in the microwave for 10 minutes. The solvent was removed under reduced pressure and the residue purified by acidic reverse phase HPLC to afford the title compound (12 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by acidic reverse phase HPLC

Sources & evidence

ORD record
ord-aa5b3adfc4df48a2bb61c3262bb83b17
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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