[SH2:1].[CH3:2][C:3]1[N:7]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]#[N:18])[CH2:13][CH2:12]2)=[O:10])[N:6]=[C:5]([C:19]([F:22])([F:21])[F:20])[CH:4]=1.N(CCO)CCO>CN(C)C=O>[CH3:2][C:3]1[N:7]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([C:17](=[S:1])[NH2:18])[CH2:13][CH2:12]2)=[O:10])[N:6]=[C:5]([C:19]([F:22])([F:20])[F:21])[CH:4]=1Hydrogen sulfide gas was passed into a solution of 1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinecarbonitrile (i.e. the product of Example 8, Step B) (9.0 g, 30 mmol) and diethanolamine (3.15 g, 30 mmol) in N,N-dimethylformamide (15 mL) at 50° C. in a flask equipped with dry-ice condenser. The hydrogen sulfide feed was stopped when the reaction mixture became saturated with hydrogen sulfide, as indicated by condensation on the cold-finger. The reaction mixture was stirred for an additional 30 minutes at 50° C. Then excess hydrogen sulfide gas was sparged into the scrubber by a subsurface nitrogen flow, and water (70 mL) was gradually added.
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