Cyclopropanemethanamine → N-tert-Butyl-3-((4-(5-chloro-4-(3-(cyclopropylmethyl)ureido)-2-ethoxybenzoyl)piperazin-1-yl)methyl)benzamide

HRID 1878357Notes

Reaction equation

HRID 1878357 reaction equation
[NH2:1][C:2]1[C:29]([Cl:30])=[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])=[C:4]([O:31][CH2:32][CH3:33])[CH:3]=1.Cl[C:35](OC1C=CC([N+]([O-])=O)=CC=1)=[O:36].[CH:47]1([CH2:50][NH2:51])[CH2:49][CH2:48]1>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]=[C:29]([Cl:30])[C:2]([NH:1][C:35]([NH:51][CH2:50][CH:47]4[CH2:49][CH2:48]4)=[O:36])=[CH:3][C:4]=3[O:31][CH2:32][CH3:33])[CH2:13][CH2:12]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 579176643-((4-(4-Amino-5-chloro-2-ethoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Product 1

HCID 57917638N-tert-Butyl-3-((4-(5-chloro-4-(3-(cyclopropylmethyl)ureido)-2-ethoxybenzoyl)piperazin-1-yl)methyl)benzamideYield 3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-((4-(4-Amino-5-chloro-2-ethoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (250 mg, 0.525 mmol) and 4-nitrophenol chloroformate (425.7 mg, 0.525 mmol) were combined and stirred in dichloromethane for 1 hour. Cyclopropylmethylamine (0.114 g, 1.6 mmol, 0.139 mL) 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 reduced pressure and purified by basic reverse phase HPLC to give the title compound (9.1 mg).

Workup

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

Sources & evidence

ORD record
ord-faa34a2ff33c4c1b8f6816f6b7ee09ab
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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