Thionyl Chloride → 2-(3-Cyano-phenoxy)-N-(5-methyl-pyrazin-2-ylmethyl)-nicotinamide

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[C:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O)#[N:2].S(Cl)(Cl)=O.[CH3:23][C:24]1[N:25]=[CH:26][C:27]([CH2:30][NH2:31])=[N:28][CH:29]=1>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH:31][CH2:30][C:27]1[CH:26]=[N:25][C:24]([CH3:23])=[CH:29][N:28]=1)=[O:11])#[N:2]

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A solution of 2-(3-Cyano-phenoxy)-nicotinic acid (0.0067 grams, 0.03 mmole) in thionyl chloride (500 μl, 6.9 mmole) was stirred at room temperature for 3 hours and concentrated under reduced pressure to give a white solid. To the residue was added pyridine (300 μl) and C-(5-Methyl-pyrazin-2-yl)-methylamine (0.0038 grams, 0.03 mmole). The mixture stood at room temperature for 3 hours and then was concentrated under reduced pressure to white solid. (0.0093 g); Anal. calcd. for C19H15N5O2: C, 66.08; H, 4.38; N, 20.26. Found: C, 56.89; H, 5.02; N, 18.31.