Chlorosuccinimide → HCID 53353298, compound

Participants

Reaction Conditions

Reaction Steps

(R)-4-(1,2-dihydroxypropan-2-yl)-N-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-3-methylbenzamide (40 mg, 0.11 mmol) was dissolved in N,N-dimethylformamide (0.57 mL) to give a light yellow solution. NCS (14 mg, 0.10 mmol) was then added at room temperature. The mixture was heated mixture at 60° C.; after 3 hr, another 15 mg of NCS was added, and the reaction completed after 1 hr. The mixture was diluted with MeOH (1 ml) and then purified by preparatory HPLC (basic mode, 20-70% ACN in water). Product-containing fractions were combined, concentrated and freeze-dried to obtain the title compound as a tan colored solid (10 mg, 23%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (t, J=7.20 Hz, 3H) 1.48 (s, 3H) 2.58 (s, 3H) 3.58-3.64 (m, 2H) 4.19 (q, J=7.24 Hz, 2H) 4.77 (br. s., 1H) 4.92 (br. s., 1H) 7.55 (d, J=8.34 Hz, 1H) 7.68 (s, 1H) 7.76-7.88 (m, 2H) 8.36 (d, J=0.76 Hz, 1H) 8.59 (d, J=1.01 Hz, 1H) 10.58 (s, 1H); ESI-MS: m/z 388 (M+H)+.

Provenance & Evidence