2-(4-Chloro-3-(dipropylamino)-5-methyl-1H-pyrazol-1-yl)-5-(8-chloronaphthalen-2-ylsulfonylcarbamoyl)benzoic acid → 3-((S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-chloro-3-(dipropylamino)-5-methyl-1H-pyrazol-1-yl)-N-(8-chloronaphthalen-2-ylsulfonyl)benzamide

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Example 91, 2-(4-chloro-3-(dipropylamino)-5-methyl-1H-pyrazol-1-yl)-5-(8-chloronaphthalen-2-ylsulfonylcarbamoyl)benzoic acid (Intermediate 193B, 50 mg, 0.083 mmol) and (S)-3-(azidomethyl)-1,2,3,4-tetrahydroisoquinoline (Intermediate 92A, 17 mg, 0.091 mmol) were converted to the title compound. 1H NMR (CDCl3, 2:1 mixture of amide rotamers) δ 9.15 (s, 1H), 8.27-8.13 (m, 1.5H), 8.07-7.80 (m, 2H), 7.72 (d, J=7.5 Hz, 1.5H), 7.61-7.51 (m, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.28-7.11 (m, 3.5H), 7.08-6.98 (m, 1H), 6.94-6.82 (m, 0.5H), 5.34 (d, J=18.5 Hz, 1H), 4.38-3.93 (m, 3H), 3.48-3.36 (m, 2H), 3.32-2.72 (m, 5H), 2.24 (s, 1H), 2.16 (s, 2H), 1.60-1.12 (m, 4H), 0.94-0.62 (m, 6H); MS(ESI+) m/z 773.2 (M+H)+.

Provenance & Evidence