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To a microwave vial containing methyl 6-(butylsulfonyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylate was added MeOH (1 mL) and hydroxylamine potassium salt (1 mL, 1.76 mmol, 1.76 M in MeOH). The solution was shaken at rt for 1 h, then acetic acid (0.102 mL, 1.8 mmol) was added to quench excess base. The solvent was then concentrated. To the resulting residue was added DMSO (1.2 mL) and after filtration, the solution underwent purification via prep-HPLC to give 6-(butylsulfonyl)-N-hydroxy-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxamide (13.3 mg, 28.3%). LC-MS: (FA) ES+ 314; 1H NMR (Methanol-d4, 300 MHz) δ 7.97 (d, J=8.1 Hz, 1H), 7.76 (d, J=7.9 Hz, 1 H), 4.59 (s, 2H), 3.70 (t, J=6.0 Hz, 2H), 3.13 (m, 4H), 1.77 (m, 2H), 1.47 (m, 2H), 0.95 (t, J=7.3 Hz, 3H).

1. customto quench excess base
2. concentrationThe solvent was then concentrated
3. additionTo the resulting residue was added DMSO (1.2 mL)
4. filtrationafter filtration
5. customthe solution underwent purification via prep-HPLC