HCID 89761699, compound → HCID 71666346, compound

Participants

Reaction Steps

Tert-butyl 4-(2-(7-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (EXAMPLE 5, 30 mg) was diluted with 0.5 mL of DCM and TFA (0.5 mL) was added. After 5 minutes, complete conversion to the desired deprotected product was observed. The material was concentrated under a vacuum and purified via reverse-phase HPLC (Column: Phenomenex 150×30 mm, 5 micron, C18 column; 0.1% TFA in CH3CN/H2O, gradient 25% to 90% over 20 min) to yield 4-(2-(1,2,3,6-tetrahydropyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.39 (m, J=17.50 Hz, 2 H) 3.19 (m, J=12.90 Hz, 2 H) 3.59 (m, J=3.80 Hz, 2 H) 3.65-3.71 (m, 2 H) 4.30 (m, J=4.90 Hz, 2 H) 5.88 (s, 1 H) 6.48 (d, J=8.41 Hz, 1 H) 7.11-7.19 (m, 2 H) 7.59 (d, J=8.12 Hz, 1 H) 7.63 (d, J=2.05 Hz, 1 H) 7.76 (dd, J=8.41, 1.66 Hz, 1 H) 8.39 (s, 1 H) 8.77 (br. s., 2 H). m/z (ESI) 524.0 (M+H)+.

Provenance & Evidence