Water → HCID 178489060, compound

Participants

Reaction Steps

(±)-Methyl 3-(5-cyano-1H-benzo[d]imidazol-2-yl)-3-(5-methoxy-7-methylindolin-4-yl)butanoate (Example 156-K) (25 mg, 0.062 mmol) was dissolved in THF (0.371 mL), water (0.124 mL) and MeOH (0.124 mL). LiOH (13 mg, 0.304 mmol) was then added and the reaction was stirred for 18 hours at room temperature. At this point, NaOH (1 mL, 2.000 mmol), MeOH (1 mL) and THF (3 mL) were added and the reaction was stirred for further 4 hours. The reaction was then concentrated and diluted with EtOAc and water. The layers were separated, the aqueous layer was adjusted to pH=1 and directly purified using RP-HPLC (HC-A) to isolate the title compound. 1H NMR (TFA salt, 400 MHz, DMSO-d6) δ ppm 11.01 (br. s., 1H) 8.11 (br. s., 1H) 7.68 (q, J=7.66 Hz, 2H) 7.22 (br. s., 1H) 6.74 (s, 1H) 5.95 (br. s., 1H) 3.55 (d, J=15.16 Hz, 1H) 3.43 (s, 1H) 3.39 (s, 3H) 2.44 (s, 3H) 1.99-2.15 (m, 3H). HRMS calcd. for C22H20N4O3 (M+H)+ 389.1614. found 389.1609.

Provenance & Evidence