Dimethylformamide → HCID 44158490, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzothiazol-2-yl-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine (211.0 mg, 0.5604 mmol), Cs2CO3 (730 mg, 2.24 mmol), and DMF (10 mL, 0.1 mol) at 0° C. was charged with methyl chloroacetate (0.0493 mL, 0.560 mmol) and then heated at 40° C. overnight. The solvent was removed in vacuo, and the material was dry-loaded onto silica gel for column chromatography, eluting with 2→5% MeOH/DCM. The fractions containing the pure ester were concentrated in vacuo and redissolved in conc. HCl. The material was transferred to a sealed tube, and heated overnight at 50° C. The HCl was removed using the corrosive pump to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.36 (br. s., 4H), 3.34 (d, J=11.4 Hz, 2H), 3.71 (d, J=9.1 Hz, 2H), 4.19 (br. s., 2H), 4.31-4.41 (m, 1H), 4.51 (br. s., 2H), 7.54-7.60 (m, 1H), 7.61-7.67 (m, 1H), 8.12-8.20 (m, 2H), 8.24 (d, J=7.1 Hz, 1H), 8.52 (d, J=1.3 Hz, 1H), 8.58-8.65 (m, 2H), 10.49 (br, s., 1H). MS (ES+): m/z=435.09 (100) [MH+]. HPLC: tR=2.24 min (ZQ2, polar—5 min).

Provenance & Evidence