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

HRID 660042Notes

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 stirred 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 2, Step C) in dichloromethane (100 mL) was cooled to −10° C., and 1 drop of N,N-dimethyl-formamide was added. A solution of oxalyl chloride (0.60 mL, 6.8 mmol) in dichloromethane (10 mL) was added dropwise to the stirred reaction mixture. The reaction mixture was stirred at −10° C. for 30 minutes more, and then allowed to warm to room temperature and stir an additional 16 h. The resulting homogeneous mixture was evaporated in vacuo, and the residue was placed under high vacuum for several hours to give 2.46 g of the title compound as a light yellow solid. This compound was of sufficient purity to use in subsequent reactions.

Workup

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

Sources & evidence

ORD record: ord-7dc227d656d04771900f40f01f180146
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084468B2

Reaction notes

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