Phosgene → (R)-1-(4-chlorobenzyl)-5-(1-chlorocarbonylpyrrolidin-2-yl)-1H-1,2,4-triazole

HRID 2063479Notes

Reaction equation

HRID 2063479 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[C:11]([C@H:12]3[CH2:16][CH2:15][CH2:14][NH:13]3)=[N:10][CH:9]=[N:8]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:28](Cl)([Cl:30])=[O:29]>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[C:11]([C@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:28]([Cl:30])=[O:29])=[N:10][CH:9]=[N:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 57650081(R)-1-(4-chlorobenzyl)-5-(pyrrolidin-2-yl)-1H-1,2,4-triazole

Product 1

HCID 57650104(R)-1-(4-chlorobenzyl)-5-(1-chlorocarbonylpyrrolidin-2-yl)-1H-1,2,4-triazoleYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-1-(4-chlorobenzyl)-5-(pyrrolidin-2-yl)-1H-1,2,4-triazole (216 mg, 0.82 mmol) and DIEA (233 mg, 1.90 mmol) in 5 mL of dry DCM was cooled to −20° C. under Ar, and a solution of phosgene (0.89 mL of 20% solution in toluene, 0.89 mmol) was added. The reaction mixture was stirred at RT for 2.5 days and the solvent was evaporated in vacuo. The residue was purified by chromatography (silica gel, hexane:EtOAc (1:1)) to give 202 mg of the desired product.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was purified by chromatography (silica gel, hexane:EtOAc (1:1))

Sources & evidence

ORD record
ord-df744902dbce4b598efd85b4b007ea08
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

Loading…