Cyclobutylamine → tert-Butyl 4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazine-1-carboxylate

HRID 408871Notes

Reaction equation

HRID 408871 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:23].[C:24](Cl)(=O)[O:25]C1C=CC([N+]([O-])=O)=CC=1.[CH:37]1([NH2:41])[CH2:40][CH2:39][CH2:38]1>ClCCl>[CH:37]1([NH:41][C:24](=[O:25])[NH:1][C:2]2[CH:22]=[CH:21][C:5]([C:6]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][CH2:9]3)=[O:7])=[CH:4][C:3]=2[F:23])[CH2:40][CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 75645CyclobutylamineHCID 821294-Nitrophenyl chloroformateHCID 58055815Tert-butyl 4-(4-amino-3-fluorobenzoyl)piperazine-1-carboxylate

Product 1

HCID 58055805tert-Butyl 4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazine-1-carboxylateYield 22.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Buty 4-(4-amino-3-fluorobenzoyl)piperazine-1-carboxylate (9.5 g, 29.41 mmol) was dissolved in dichloromethane (100 mL) and 4-nitrophenyl carbonochloridate (5.93 g, 29.41 mmol) was added. The reaction mixture was stirred for 20 hours and cyclobutylamine (7.5 mL, 88.2 mmol) added. After 2 hours, the reaction mixture was chromatographed on silica (eluting with dichloromethane to dichloro-methane/ethyl acetate) to give the title compound (2.8 g). MS (ESI) m/z: 421.0 [M+H]+

Workup

  1. waitAfter 2 hours
  2. customthe reaction mixture was chromatographed on silica (eluting with dichloromethane to dichloro-methane/ethyl acetate)

Sources & evidence

ORD record
ord-de8ded0b1cb840e29a5b01e3b37f54d4
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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