2-Chloroethyl chloroformate → 2-Chloroethyl 5-{[2-(4-{[(2-chloroethoxy)carbonyl]amino}phenyl)propanoyl]amino}-3-cyclopropyl-1H-pyrazole-1-carboxylate

HRID 1282023Notes

Reaction equation

HRID 1282023 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:20])[C:9]([NH:11][C:12]2[CH:16]=[C:15]([CH:17]3[CH2:19][CH2:18]3)[NH:14][N:13]=2)=[O:10])=[CH:4][CH:3]=1.[Cl:21][CH2:22][CH2:23][O:24][C:25](Cl)=[O:26]>N1C=CC=CC=1>[Cl:21][CH2:22][CH2:23][O:24][C:25]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:20])[C:9]([NH:11][C:12]2[N:13]([C:25]([O:24][CH2:23][CH2:22][Cl:21])=[O:26])[N:14]=[C:15]([CH:17]3[CH2:19][CH2:18]3)[CH:16]=2)=[O:10])=[CH:6][CH:7]=1)=[O:26]

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformateHCID 12043812HCID 12043812, compound

Product 1

HCID 120438162-Chloroethyl 5-{[2-(4-{[(2-chloroethoxy)carbonyl]amino}phenyl)propanoyl]amino}-3-cyclopropyl-1H-pyrazole-1-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

154 mg (0.57 mmol) of 2-(4-aminophenyl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)propanamide were dissolved in 1.9 ml of dry pyridine at 4° C. under argon atmosphere and 0.12 ml (1.148 mmol) of 2-chloroethylchloroformate were added dropwise. After 2.5 hours the reaction mixture was poured into ice and the precipitate solid collected by filtration, affording 225 mg (82% yield) of the title compound.

Workup

  1. additionAfter 2.5 hours the reaction mixture was poured into ice
  2. filtrationthe precipitate solid collected by filtration

Sources & evidence

ORD record
ord-4822a8ab1b914c15988e049e4149e4a5
Source dataset
uspto-grants-2002_09
Patent number
US06455559B1

Reaction notes

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