3-Amino-1-propanol → 6-[(2-{[(3R)-3-Methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methyl benzo[b]thiophene-3-carboxylic acid 3-hydroxypropylamide

Participants

Reaction Steps

This material was prepared from the reaction of 6-[(2-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]-2-methylbenzo[b]thiophene-3-carboxylic acid 123b (130 mg, 0.278 mmole) with 3-amino-1-propanol (106 μL, 1.39 mmole), N,N-diisopropylethylamine (0.15 mL, 0.83 mmole), and HBTU (263 mg, 0.694 mmole) in a manner similar to that previously described for example 117 to give a yellow solid (34 mg, 23%). 1H NMR (DMSO-d6, 300 MHz) δ8.58 (1H, d, J=5.27 Hz), 8.36 (1H, t, J=5.65 Hz), 8.06 (1H, s), 7.96 (1H, d, J=2.07 Hz), 7.83 (1H, d, J=8.85 Hz), 7.33 (1H, dd, J=2.07, 8.85 Hz), 6.75 (1H, d, J=5.27 Hz), 4.51 (1H, t, J=5.18 Hz), 4.13-3.82 (3H, m), 3.62 (2H, m), 3.50 (2H, m), 3.39-3.30 (2H, m), 3.27, 3.24 (3H, s), 2.60 (3H, s), 2.18-1.93 (2H, m), 1.71 (2H, quintet, J=6.6 Hz).

Provenance & Evidence