Tris(hydroxymethyl)aminomethane → HCID 71086351, compound

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Example 124, 3-(N-butyl-4-chloro-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-pyrazole-3-carboxamido)propanoic acid (Intermediate 158B, 20 mg, 0.026 mmol) and 2-amino-2-(hydroxymethyl) propane-1,3-diol (J. T. Baker, 10 mg, 0.083 mmol) were converted to the title compound (4 mg, 18%). 1H NMR (CD3OD, 1.5:1 mixture of amide rotamers) δ 8.73 (br s, 1H), 8.17-7.94 (m, 7H), 7.75-7.65 (m, 3H), 7.23-7.09 (m, 3.5H), 6.96-6.83 (m, 0.5H), 4.61-4.40 (m, 1H), 4.38-3.91 (m, 3H), 3.73-3.66 (m, 3H), 3.66-3.49 (m, 4H), 3.02-2.97 (m, 1H), 2.89-2.79 (m, 2H), 2.75-2.60 (m, 2H), 2.56 (t, J=6.9 Hz, 0.5H), 2.38-2.31 (m, 2H), 2.28-2.23 (m, 1.5H), 1.57-1.18 (m, 4H), 1.14-0.84 (m, 3H), 0.76 (t, J=7.3 Hz, 1H), 0.68 (t, J=7.3 Hz, 1H); MS(ESI+) m/z 859.4 (M+H).

Provenance & Evidence