Chloroacetic Acid → HCID 69318869, compound

Participants

Reaction Steps

Compound 152 was prepared according to General Method 5 (EXAMPLE 2) from (3R)-3,4-dihydro-8-isopropoxy-3-isopropyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (16 mg, 0.05 mmol) and NaBH4 pellets (>10 equiv) in 0.5 g chloroacetic acid to afford 11 mg (58%) of (3R)-4-(2-chloroethyl)-3,4-dihydro-8-isopropoxy-3-isopropyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline. This material (11 mg, 0.03 mmol) was carried on according to General Method 4 (EXAMPLE 1) by treatment with 4 mL of 1:1 acetic acid:concentrated HCl (0.02M) heated at 90° C. for 4 h to afford Compound 152. 1H NMR (500 MHz, CDCl3) 12.06 (bs, 1H), 7.13 (s, 1H), 7.12 (d, J=8.8, 1H), 6.98 (d, J=8.8, 1H), 4.53 (dd, J=10.7, 1.5, 1H), 3.88 (dd, J=10.7, 2.4, 1H), 3.82 (m, 1H), 3.71 (m, 1H), 3.63 (m, 1H), 3.49 (m, 1H), 2.93 (m, 1H), 1.82 (m, 1H), 0.99 (d, J=10.3, 3H), 0.98 (d, J=10.3, 3H).

Provenance & Evidence