3-Bromo-5,6,7,8-tetrahydro-1,6-naphthyridine → 1-(2-(3-Bromo-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)-4-(naphthalen-2-ylsulfonylcarbamoyl)phenyl)-N,N-dibutyl-4-chloro-5-methyl-1H-pyrazole-3-carboxamide

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Intermediate 93B, 2-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoic acid (Intermediate 91F, 25 mg, 0.040 mmol) and 3-bromo-5,6,7,8-tetrahydro-1,6-naphthyridine (D-L Chiral, 9 mg, 0.044 mmol) were converted to the title compound (16 mg, 45%) following purification by preparative HPLC. 1H NMR (1:1 CD3OD:CDCl3, 1.5:1 mixture of amide rotamers) δ ppm 8.69-8.65 (m, 1H), 8.47-8.41 (m, 1H), 8.21-8.16 (m, 1H), 8.09-8.05 (m, 2H), 8.04-8.00 (m, 1H), 7.99-7.95 (m, 1.5H), 7.94-7.90 (m, 1H), 7.78-7.74 (m, 0.5H), 7.66-7.57 (m, 1.5H), 7.53-7.43 (m, 1.5H), 4.79-4.73 (m, 1H), 4.57-4.51 (m, 1H), 3.71-3.61 (m, 1.5H), 3.58-3.39 (m, 1H), 3.31-2.85 (m, 5.5H), 2.31 (s, 1.5H), 2.28 (s, 1.5H), 1.57-1.02 (m, 8H), 0.93 (dt, J=14.4, 7.4 Hz, 3H), 0.79 (t, J=7.4 Hz, 1.5H), 0.74 (t, J=7.4 Hz, 1.5H); MS(ESI+) m/z 821.0 (M+H)+.

Provenance & Evidence