Benzylamine → HCID 59224407, compound

Participants

Reaction Conditions

Reaction Steps

3-(1,4-Dioxa-spiro[4.5]dec-8-ylamino)-8-methyl-isoquinoline-6-carboxylic acid (100.0 mg, 0.29 mmol) in 5 ml DMA was treated with a HATU (240.0 mg, 0.63 mmol) and triethylamine (192.0 mg, 1.89 mmol) for 1 hour at room temperature. After 1 hour, benzylamine (74.5 mg, 0.69 mmol) was added and the mixture was heated to 50° C. for 2 hours. The reaction was completed by LC/MS monitoring. The solvent DMA was evaporated under vacuum, and the crude was dissolved in CH2Cl2 and washed with NaHCO3 aqueous (10%) to remove the by-products from HATU. The crude residue was purified by a silica gel column to give 119.0 mg (94.4%). 1H NMR (400 MHz, CHLOROFORM-d) ppm 1.59-1.75 (m, 2H), 1.78-1.95 (m, 4H), 2.01-2.12 (m, 2H), 2.64 (s, 3H), 3.39-3.55 (m, J=4.28 Hz, 1H), 3.91-4.04 (m, 4H), 4.69 (d, J=5.54 Hz, 2H, 6.62 (s, 1H), 6.94 (s, 1H), 7.34-7.46 (m, 5H), 7.87 (s, 1H), 8.85 (s, 1H).

Provenance & Evidence