Triethylamine → HCID 178469348, compound

Reaction equation

Cl.[CH3:2][C:3]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:11]2[C:6](=[CH:7][C:8]([NH2:12])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:13].C([N:21](CC)CC)C.[N:26]1[CH:31]=[CH:30][N:29]=[CH:28][C:27]=1[C:32](Cl)=O>C(Cl)Cl>[CH3:2][C:3]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:11]2[C:6](=[CH:7][C:8]3[NH:12][C:32]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][N:26]=4)=[N:21][C:9]=3[CH:10]=2)[NH:5][C:4]1=[O:13]

Participants

Procedure

5.0 g. (18.5 mmol) 3-methyl-3-ethoxycarbonyl-6-aminoindolin-2-one hydrochloride are suspended in 60 ml. methylene chloride and mixed with 12.5 ml. (90.4 mmol) triethylamine. 6.4 g. (45.2 mmol) pyrazine-2-carboxylic acid chloride are then added portionwise, while cooling with ice, and the reaction mixture is further stirred for 3 hours. The reaction mixture is evaporated, worked up with water, filtered off with suction and purified by column chromatography elution agent: methylene chloride/methanol 99:1 v/v). There are obtained 4.0 g. (65% of theory) of the title compound; m.p.