Water → HCID 57917713, compound

HRID 1878385Notes

Reaction equation

HRID 1878385 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][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])[C@H:10]([CH3:28])[CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:31].Cl[C:33](OC1C=CC([N+]([O-])=O)=CC=1)=[O:34].[CH:45]1([CH2:48][NH2:49])[CH2:47][CH2:46]1.O>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:29]=[CH:30][C:2]([NH:1][C:33]([NH:49][CH2:48][CH:45]4[CH2:47][CH2:46]4)=[O:34])=[C:3]([F:31])[CH:4]=3)[CH2:9][C@H:10]2[CH3:28])[CH:16]=1)([CH3:23])([CH3:22])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 57917582HCID 57917582, compound

Product 1

HCID 57917713HCID 57917713, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-3-((4-(4-Amino-3-fluorobenzoyl)-2-methylpiperazin-1-yl)methyl)-N-tert-butylbenzamide (119 mg, 0.275 mmol) and 4-nitrophenol chloroformate (56 mg, 0.275 mmol) were combined and stirred in dichloromethane for 1 hour. Cyclopropanemethylamine (56.8 mg, 0.8 mmol, 0.0694 mL) was added and the reaction was stirred for a further 30 minutes. Water was added and the reaction mixture was flushed through a hydrophobic frit. The organic phase was concentrated under reduced pressure and purified by basic reverse phase HPLC to afford the title compound (19.8 mg). MS (ES) m/z 524.7 [M+H]+

Workup

  1. customthe reaction mixture was flushed 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-deca6690ed6748968da0216b2ff2adbf
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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