4-Methylmorpholine → HCID 86601024, compound

Participants

Reaction Steps

Part A. 2′-(6-cyano-1-ethyl-1H-indol-3-ylmethyl)-4-methyl-5′-(methylcarbamoylmethyl-carbamoyl)-biphenyl-2-carboxylic acid: A solution of the compound of Example 37, Part D (0.1 g, 0.19 mmol), N-methylglycinamide (0.04 mg, 0.28 mmole), NMM (0.1 ml, 0.9 mmol) and BOP reagent (0.13 g, 0.28 mmol) in 1.5 ml DMF was stirred for 3 days at rt in a screw cap test tube. Reaction was diluted with water and extracted 3× with EtOAc. Combined extracts were washed with water and brine then dried over anh. Na2SO4, filtered and evaporated. Chromatography on silica gel provided the amide product (99 mg. 85%). 1H NMR (500 MHz, CDCl3) δ ppm 1.37 (t, J=7.15 Hz, 3H) 2.41 (s, 3H) 2.83 (d, J=4.40 Hz, 3H) 3.77 (s, 2H) 4.03 (m, 4H) 6.06 (s, 1H) 6.66 (s, 1H) 6.75 (t, J=5.22 Hz, 1H) 6.97 (d, J=7.70 Hz, 1H) 7.05 (m, 2H) 7.17 (dd, J=15.95, 8.25 Hz, 2H) 7.24 (m, 5H) 7.50 (s, 1H) 7.56 (s, 1H) 7.64 (d, J=6.05 Hz, 1H) 7.83 (s, 1H). LC/MS m/z 599.4)M+H)+.

Provenance & Evidence