ClC1C=[CH:4][N:5](C(OC)=O)NC=1.[Cl:12][C:13]1[N:14]=[CH:15][C:16]([C:19]([OH:21])=O)=[N:17][CH:18]=1.ClC1N=CC(C(Cl)=O)=NC=1.S(Cl)(Cl)=O.C(Cl)(=O)C(Cl)=O.CN>O1CCCC1>[Cl:12][C:13]1[N:14]=[CH:15][C:16]([C:19]([NH:5][CH3:4])=[O:21])=[N:17][CH:18]=1Methyl 5-chloro-2-pyridazinecarboxylate (CAS #33332-25-1) is hydrolyzed to the corresponding carboxylic acid, 5-chloropyrazine-2-carboxylic acid. This acid is then converted to the corresponding acid chloride, 5-chloropyrazine-2-carbonyl chloride, by treatment with either thionyl chloride or oxalyl chloride. This acid chloride is then treated with a 2 M solution of methylamine in tetrahydrofuran to provide 5-chloro-N-methylpyrazine-2-carboxamide. The procedure of Example 48 is then repeated, substituting 5-chloro-N-methylpyrazine-2-carboxamide in place of 6-chloro-N-methyl-3-pyridinecarboxamide to give (R)—N-methyl-5-(2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazol-6-yloxy)pyrazine-2-carboxamide.
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