Hydrochloric Acid → HCID 86666036, compound

HRID 469714

Reaction equation

[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(N(CC)C(C)C)(C)C.[Cl:28][C:29]1[C:30](F)=[N:31][CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1>CS(C)=O>[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:30]2[C:29]([Cl:28])=[CH:34][C:33]([C:35]([F:38])([F:36])[F:37])=[CH:32][N:31]=2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

To a vial containing (S)-pyrrolidine-2-carboxylic acid (4-tert-butyl-thiazol-2-yl)-amide; hydrochloride (0.212 g; 0.731 mmol) in dimethylsulfoxide (2 mL) is added N,N-diisopropylethylamine (0.127 mL; 0.731 mmol) and 3-chloro-2-fluoro-5-trifluoromethylpyridine (0.096 mL; 0.731 mmol). The mixture is heated at 100° C. for 1 hour in an oil bath and then cooled to room temperature. The crude mixture is filtered and purified by preparative HPLC chromatography. Product fractions are pooled and concentrated in vacuo to afford title compound. ESI m/z 433 [M+H]+

Workup

temperaturecooled to room temperature
filtrationThe crude mixture is filtered
custompurified by preparative HPLC chromatography
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8bcb9c11fc4f4614bdb451cb936af102
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629157B2

Linked notes

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