Cyclopropanemethanamine → N-tert-Butyl-3-((4-(4-(3-(cyclopropylmethyl)ureido)-3-fluorobenzoyl)-2-(fluoromethyl)piperazin-1-yl) methyl)benzamide

HRID 1878392Notes

Reaction equation

HRID 1878392 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][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])[CH:10]([CH2:28][F:29])[CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:32].Cl[C:34](OC1C=CC([N+]([O-])=O)=CC=1)=[O:35].[CH:46]1([CH2:49][NH2:50])[CH2:48][CH2:47]1>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:30]=[CH:31][C:2]([NH:1][C:34]([NH:50][CH2:49][CH:46]4[CH2:48][CH2:47]4)=[O:35])=[C:3]([F:32])[CH:4]=3)[CH2:9][CH:10]2[CH2:28][F:29])[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 579176673-((4-(4-Amino-3-fluorobenzoyl)-2-(fluoromethyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Product 1

HCID 57917629N-tert-Butyl-3-((4-(4-(3-(cyclopropylmethyl)ureido)-3-fluorobenzoyl)-2-(fluoromethyl)piperazin-1-yl) methyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((4-(4-amino-3-fluorobenzoyl)-2-(fluoromethyl)piperazin-1-yl)-methyl)-N-tert-butylbenzamide (150 mg, 0.34 mmol) in dichloromethane (4 mL) at room temperature was added 4-nitrophenyl chloroformate (71.4 mg, 0.354 mmol). The reaction mixture was stirred at room temperature for 1 hour before the addition of cyclopropane-methylamine (150 μL). The mixture was stirred at room temperature overnight before being applied to a silica carbonate column. The eluant was concentrated under reduced pressure and redissolved in methanol. Purification by basic reverse phase HPLC gave the title compound (2 mg), MS (ESI) m/z 542.5 [M+H]+

Workup

  1. concentrationThe eluant was concentrated under reduced pressure
  2. dissolutionredissolved in methanol
  3. customPurification by basic reverse phase HPLC

Sources & evidence

ORD record
ord-088e38c8f3974257ba63d6929999d006
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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