[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:4]=2[S:5][CH:6]=1.Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[OH2:20].[C:21](=[O:24])([O-:23])[O-].[Na+].[Na+].CN1C[CH2:31][CH2:30][C:29]1=[O:33]>>[C:29]([OH:33])(=[O:20])/[CH:30]=[CH:31]\[C:21]([OH:23])=[O:24].[F:11][C:8]1[CH:9]=[CH:10][C:3]2[C:2]([NH:1][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:6][S:5][C:4]=2[CH:7]=1A solution of 3-amino-6-fluorobenzo[b]thiophene (7 g) and 4-chloropyridine hydrochloride (7 g) in 200 mL 1-methyl-2-pyrrolidinone was stirred one hour at 80°-85° C. and thereafter cooled, stirred with water, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was washed successively with water and a saturated sodium chloride solution and thereafter dried (anhydrous magnesium sulfate), filtered and concentrated to 10 g of a dark oil. This oil was eluted through silica with 10% methanol in dichloromethane via HPLC to yield 4.7 g of a brown solid, m.p. 102°-106° C. The solid was converted to the maleate salt in 20% methanol in ether and immediately thereafter recrystallized from 20% methanol in ether to yield 2.9 g of white crystals, m.p. 172°-174° (dec.).
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