HCID 86671482, compound → HCID 68312760, compound

Participants

Reaction Steps

A solution of methanesulfonic acid 2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-methanesulfonyloxymethyl-4-methylpentyl ester (194 mmol) in isopropylamine (2 mL) was heated at 150° C. for 33 h using microwave irradiation. After cooling to RT, the crude reaction mixture was evaporated and then purified by column chromatography (C18, gradient 30-55% MeOH in 0.5% TFA/H2O) and then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3/MeOH affording 301 as a colourless foam (95 mg, 100% over 2 steps). LCMS (Method K): RT 3.29 min [M+H]+ 479.2. 1H NMR (CD3OD, 400 MHz): δ 8.41 (1H, d, J=9.0 Hz), 7.69 (1H, s), 6.67 (1H, bd, J=9.0 Hz), 6.51 (1H, bs), 5.84 (1H, septet, J=6.6 Hz), 4.51 (4H, s), 4.44-4.37 (4H, m), 3.49-3.42 (1H, m), 2.36 (3H, s), 2.17 (2H, d, J=6.9 Hz), 1.72 (1H, nonet, J=6.8 Hz), 1.52 (6H, d, J=6.6 Hz), 1.25 (6H, d, J=6.5 Hz), 0.92 (6H, d, J=6.8 Hz)

Provenance & Evidence