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

HRID 408852Notes

Reaction equation

HRID 408852 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[S:16][CH:17]=[C:18]([C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:19]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:29].Cl[C:31](OC1C=CC([N+]([O-])=O)=CC=1)=[O:32].[CH:43]1([CH2:46][NH2:47])[CH2:45][CH2:44]1>ClCCl.O>[C:23]([NH:22][C:20]([C:18]1[N:19]=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]3[CH:27]=[CH:28][C:2]([NH:1][C:31]([NH:47][CH2:46][CH:43]4[CH2:45][CH2:44]4)=[O:32])=[C:3]([F:29])[CH:4]=3)[CH2:9][CH2:10]2)[S:16][CH:17]=1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 666616772-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylthiazole-4-carboxamide

Product 1

HCID 66661572N-tert-Butyl-2-((4-(4-(3-(cyclopropylmethyl)ureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)thiazole-4-carboxamideYield 4.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylthiazole-4-carboxamide (100 mg, 0.238 mmol) and 4-nitrophenol chloroformate (48 mg, 0.238 mmol) were combined and stirred in dichloromethane for 1 hour at room temperature. Cyclopropylmethylamine (50.9 mg, 0.715 mmol, 62 μl) 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 vacuum and purified by acidic reverse phase HPLC to afford the title compound (5 mg). MS (ESI) m/z 517.3 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-8995b7b89ce04f6887902198d245c9c1
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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