[CH2:1]([S:5](Cl)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].Cl.[N:10]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][C:14]=2[CH:13]=[CH:12][C:11]=1[C:20]([O:22][CH3:23])=[O:21]>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH2:1]([S:5]([N:16]1[CH2:17][CH2:18][C:19]2[N:10]=[C:11]([C:20]([O:22][CH3:23])=[O:21])[CH:12]=[CH:13][C:14]=2[CH2:15]1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]To a microwave vial containing n-butanesulfonyl chloride (0.0352 g, 0.225 mmol), was added methyl 5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylate hydrochloride (0.0288 g, 0.15 mmol), TEA (0.167 mL, 1.2 mmol), DMAP (1.83 mg, 0.015 mmol), and DMF (2 mL). The mixture was shaken at rt for 13 h. The solvent was then completely evaporated to yield a solid. LC-MS: (FA) ES+ 313.
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