Oxalyl chloride → 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride

HRID 2043767Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[S:17][CH:18]=[C:19]([C:21](O)=[O:22])[N:20]=3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1.C(Cl)(=O)C([Cl:31])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[S:17][CH:18]=[C:19]([C:21]([Cl:31])=[O:22])[N:20]=3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylic acid (2.55 g, 5.87 mmol) (i.e. the product of Example 19, Step C) in 100 mL of dichloromethane was cooled to −10° C. and added 1 drop of N,N-dimethylformamide. The reaction mixture was treated with a dropwise addition of a solution of oxalyl chloride (0.60 mL, 6.8 mmol) in 10 mL of dichloromethane. The reaction mixture was stirred at −10° C. for 30 minutes, allowed to warm to room temperature and stirred an additional 16 h. The resulting homogeneous mixture was evaporated in vacuo and the residue placed under high vacuum for several hours to give 2.46 g of the title compound as a light yellow solid.

Workup

temperatureto warm to room temperature
stirringstirred an additional 16 h
customThe resulting homogeneous mixture was evaporated in vacuo
waitthe residue placed under high vacuum for several hours

Sources & evidence

ORD record: ord-8f128edb93f5483bacf5359ede1288a2
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586611B2

Reaction notes

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