Dimethylformamide → HCID 59239414, compound

Participants

Reaction Steps

(S)-1-ethyl-3-(4-(4-(3-ethylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0473 g, 0.115 mmol) in dry N,N-Dimethylformamide (0.60 mL, 7.7 mmol) was added N,N-Diisopropylethylamine (0.0636 mL, 0.365 mmol) followed by Trifluoromethanesulfonyl chloride (0.01940 mL, 0.1822 mmol). The reaction mixture was stirred for overnight. The reaction mixture was concentrated and was chromatographed through silica gel (4 g, 0-100% EtOAc in heptane followed by 10% MeOH in dichloromethane). The trifluoromethanesulfonamide was isolated and purified by HPLC. (S)-1-ethyl-3-(4-(4-(3-ethylmorpholino)-7-(trifluoromethylsulfonyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (xi): 1H NMR (400 MHz, DMSO) δ 8.66 (s, 1H), 8.16 (d, J=8.7, 2H), 7.48 (d, J=8.8, 2H), 6.18 (t, J=5.6, 1H), 4.68-4.52 (m, 2H), 4.01 (s, 1H), 3.82 (dd, J=26.3, 11.2, 3H), 3.69 (t, J=12.6, 3H), 3.54 (t, J=11.1, 1H), 3.49-3.38 (m, 1H), 3.18-3.06 (m, 2H), 2.87 (s, 1H), 2.75 (d, J=16.4, 1H), 1.80 (dd, J=11.3, 6.9, 2H), 1.06 (t, J=7.2, 3H), 0.83 (t, J=7.4, 3H). LC/MS-m/z+543.2 (M+H)+

Provenance & Evidence