4-Bromo-2-methylphenyl isocyanate → N-(4-Bromo-2-methylphenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide

HRID 2405342Notes

Reaction equation

HRID 2405342 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:10][CH2:9][C@@H:8]([CH2:11][C:12]([NH:14][NH2:15])=[O:13])[CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[C:19]([CH3:26])[CH:18]=1>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:15][NH:14][C:12](=[O:13])[CH2:11][C@@H:8]2[CH2:9][CH2:10][N:6]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[CH2:7]2)=[O:25])=[C:19]([CH3:26])[CH:18]=1

Participants

4

Reactant 2

HCID 27355944-Bromo-2-methylphenyl isocyanateHCID 673540782-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide

Product 1

HCID 71087270N-(4-Bromo-2-methylphenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide (800 mg, 3.79 mmol) in dry dichloromethane (5 mL) was added 4-bromo-1-isocyanato-2-methylbenzene (803 mg, 3.79 mmol). The reaction was allowed to progress for 1 h at room temperature (became a thick suspension that could not be stirred). The reaction mixture was diluted with dichloromethane (10 mL) and the precipitate was collected by filtration. A second crop was obtained by filtration and the two crops were combined, rinsed with minimal dichloromethane and dried to constant weight under high vacuum to provide the title product (1.54 g, 3.64 mmol, 96% yield) as a white solid. MS(ES)+ m/e 422.9 [M+H]+. This material was 76% pure by LCMS (UV214) and was used as is in the next step.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customA second crop was obtained by filtration
  3. washrinsed with minimal dichloromethane
  4. customdried to constant weight under high vacuum

Sources & evidence

ORD record
ord-cea5e2d6ac5749d0a07ed92b8f0c6119
Source dataset
uspto-grants-2014_08
Patent number
US08802864B2

Reaction notes

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