Water → HCID 178461179, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-{trans-3-[(S)-2-methylpiperidin-1-yl]cyclobutyl}-1,3-benzothiazole-6-carboxylate (Example 143A, 2.0 g, 5.8 mmol) was dissolved in methanol (600 mL), followed by H2O (300 mg, 16.7 mmol) and sodium methoxide (1.4 g, 26 mmol) at 23° C. The reaction mixture was then allowed to stir at 23° C. for 1 day. Solvent and excess of water were removed. HCl (2N) was added to make the mixture slightly acidic (pH ˜5-6). Excess of water was removed. The solid was triturated with CH2Cl2/MeOH, and filtrated. The solvents of the filtrate were removed under vacuum. The residue was treated with CH2Cl2 and filtrated again. Removal of the solvent gave the desired product as an off-white solid (2.13 g, 100%). 1H NMR (300 MHz, CD3OD): δ=8.54 ppm (d, J=1.3 Hz, 1H), 8.11 (dd, J=8.9, 1.3 Hz, 1H), 7.91 (d, J=8.9 Hz, 1H), 4.00 (m, 1H), 3.80 (m, 1H), 2.70-3.10 (m, 7H), 2.00 (m, 2H), 1.80 (m, 2H), 1.65 (m, 2H), 1.41 (d, J=6.8 Hz, 3H). MS (ESI, M+H+): 331.0.

Provenance & Evidence