Ethanol → HCID 178434683, compound

Participants

Reaction Conditions

Reaction Steps

To 6-(tert-butylsulfonyl)-4-chloro-7-(2,2-difluoroethoxy)quinoline (85 mg, 0.234 mmol) and 3,4-dimethyl-1H-pyrazol-5-amine (33.8 mg, 0.304 mmol) in a microwave vial was added EtOH (779 μl) followed by 1 drop of 1N aq HCl (8.52 mg, 0.234 mmol). The vial was sealed and heated to 80° C. behind a blast shield overnight. LCMS showed full conversion to product. Concentrated reaction and triturated resulting residue with ˜2 mL of MeCN using ˜1 min of sonication. Filtered resulting solid, rinsing with MeCN, and dried under vacuum resulting in the product 6-(tert-butylsulfonyl)-7-(2,2-difluoroethoxy)-N-(3,4-dimethyl-1H-pyrazol-5-yl)quinolin-4-amine, hydrochloride (93.5 mg, 0.197 mmol, 84% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.70 (s, 1H), 11.25 (br. s., 1H), 9.26 (br. s., 1H), 8.51 (d, J=7.07 Hz, 1H), 7.57 (s, 1H), 6.67 (d, J=7.33 Hz, 1H), 6.47 (tt, J=3.28, 53.81 Hz, 1H), 4.63 (td, J=3.16, 14.46 Hz, 2H), 2.24 (s, 3H), 1.84 (s, 3H), 1.34 (s, 9H). MS: m/z: 439.3 [M+H]+.

Provenance & Evidence