Acetic Acid → HCID 69316833, compound

Participants

Reaction Steps

This compound was prepared according to General Method 6 (EXAMPLE 3) from (3R)-3,4-dihydro-8-isopropoxy-3-methyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (16 mg, 0.049 mmol) and NaBH4 pellets (large excess, >10 equiv) in 5 mL acetic acid (0.01 M stirred at rt for 12 h, to afford 18 mg (100%) of (3R)-4-ethyl-3,4-dihydro-8-isopropoxy-3-methyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline. This material (18 mg, 0.050 mmol) was carried on according to General Method 4 (EXAMPLE 1) by treatment with 2.5 mL acetic acid and 2.5 mL concentrated HCl and heated at 90° C. for 4 h to afford 9 mg (57%) of Compound 103, after purification by column chromatography (3:1 hexanes: EtOAc to 1:1 hexanes:EtOAc, gradient elution). 1H NMR (500 MHz, CDCl3) δ 12.02 (bs, 1H), 7.12 (s, 1H), 7.04 (d, J=8.8, 1H), 6.97 (d, J=9.3, 1H), 4.10 (dd, J=10.2, 3.4, 1H), 4.02 (dd, J=10.3, 2.9, 1H), 3.53 (m, 1H), 3.43 (m, 1H), 3.32 (m, 1H), 1.22 (d, J=6.9, 3H), 1.18 (t, J=7.1, 3H).

Provenance & Evidence