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

HRID 2405310Notes

Reaction equation

HRID 2405310 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])=[CH:19][CH:18]=1.[N-]=C=O>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])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 756094-Bromophenyl isocyanateHCID 105034IsocyanateHCID 673540782-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide

Product 1

HCID 71087933N-(4-bromophenyl)-2-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamideYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask under nitrogen, a solution of 2-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide (52.6 g, 249 mmol) in dichloromethane (356 mL) was cooled to 0° C. and 4-bromophenylisocyanate (49.3 g, 249 mmol) was added. Once the isocyanate dissolved, the cooling bath was removed and the reaction was allowed to warm to room temperature and was stirred for 27 h. White precipitate formed quickly. The reaction was filtered to collect the white precipitate, washed with 50 mL cold dichloromethane, and air dried. The white solid was washed with additional cold dichloromethane (300 mL) and dried under vacuum suction overnight to provide the title compound (108.29 g, 63% pure, 167 mmol, 67% yield). MS(ES)+ m/e 409.2, 411.2 [M+H]+.

Workup

  1. customthe cooling bath was removed
  2. customWhite precipitate
  3. customformed quickly
  4. filtrationThe reaction was filtered
  5. customto collect the white precipitate
  6. washwashed with 50 mL cold dichloromethane, and air
  7. customdried
  8. washThe white solid was washed with additional cold dichloromethane (300 mL)
  9. customdried under vacuum suction overnight

Sources & evidence

ORD record
ord-fde13c0f722642aca66dc8691afe7830
Source dataset
uspto-grants-2014_08
Patent number
US08802864B2

Reaction notes

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