Hydrochloric Acid → HCID 54724773, compound

Reaction equation

[OH:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH:11]([CH3:13])[CH3:12])=[CH:8][CH:9]=2)[S:4][C:3]=1[C:14]([O:16]C)=O.[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[C:23]([CH:26]=1)[C:24]#[N:25].Cl>>[C:24]([C:23]1[CH:26]=[C:19]([NH:18][C:14]([C:3]2[S:4][C:5]3=[N:6][C:7]([CH:11]([CH3:12])[CH3:13])=[CH:8][CH:9]=[C:10]3[C:2]=2[OH:1])=[O:16])[CH:20]=[CH:21][C:22]=1[O:27][CH2:28][C:29]([CH3:31])([CH3:30])[CH3:32])#[N:25]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 178227345-Amino-2-neopentyloxybenzonitrile

HCID 54724774HCID 54724774, compound

Product 1

HCID 54724773HCID 54724773, compoundYield 22.3%

Procedure

Methyl 3-hydroxy-6-isopropylthieno[2,3-b]pyridine-2-carboxylate (1.6 g) and 5-amino-2-neopentyloxybenzonitrile (2.6 g) were stirred at 170° C. for 2 hr. Then the reaction mixture was treated with diluted hydrochloric acid and the organic layer was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained crystals were recrystallized from water-containing dimethylformamide to give the title compound (0.6 g). melting point: 211-212° C.