Triethylamine → HCID 45273206, compound

Participants

Reaction Steps

Indole-5-carboxylic acid (30 mg, 0.19 mmol), EDCI (45 mg, 0.24 mmol), HOBT (31 mg, 0.24 mmol), triethylamine (31 mg, 0.32 mmol), and compound 39a (50 mg, 0.16 mmol) were dissolved in dry CH2Cl2 (10 ml) and stirred at ambient temperature overnight. The mixture was poured into sat. NaHCO3 and extracted with dichloromethane. The organic extract was dried (Na2SO4), filtered and concentrated to yield the crude product. Column chromatography afforded 40a (26 mg, 37%). 1H NMR (400 MHz, CDCl3) δ 0.87 (t, 3H, J=7.2 Hz), 1.40-1.54 (m, 3H), 1.93 (d, 1H, J=10.0 Hz), 2.45-2.78 (m, 14H), 2.86-2.91 (m, 1H), 3.70 (m, 4H), 6.45 (d, 1H, J=2.0 Hz), 6.55-6.58 (m, 2H), 6.87 (d, 1H, J=8.0 Hz), 7.21-7.24 (m, 2H), 7.33 (d, 1H, J=8.4 Hz), 7.71 (s, 1H), 8.79 (1H, bs). The free base of 40a was converted into oxalate salt. m.p. 194-199° C. Anal. [C28H38N4O.2.0(COOH)2] C, H, N.

Provenance & Evidence