Methanol → HCID 118161685, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (±)-6-(3-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-1-isopropyl-1H-pyrazol-5-yl)-4-methylhexahydro-2H-cyclopropa[4,5]cyclopenta[1,2-b][1,4]oxazin-3(6bH)-one (0.040 g, 0.092 mmol) in tetrahydrofuran (5 mL) was added borane tetrahydrofuran complex (5 mL, 5 mmol). The reaction mixture was heated at 70° C. for 2 h under nitrogen. Methanol was added and the resulting solution was concentrated in vacuo. Purification by preparative HPLC afforded a 1.5:1 mixture of diastereomers (15 mg, 39%). LCMS (ESI): [MH]+=401.9 1H NMR (400 MHz, Methanol-d4) δ: 8.52 (d, J=3.6 Hz, 1 H), 8.32 (s, 1 H), 8.13 (s, 1 H), 6.31 (s, 0.6 H), 6.22 (s, 0.4 H), 4.85-4.82 (m, 1H), 4.06-4.02 (m, 1 H), 3.85-3.70 (m, 1.6 H), 3.50-3.45 (m, 0.4 H), 3.40-3.30 (m, 0.6 H), 3.20-3.17 (m, 0.4 H), 2.90-2.85 (m, 0.6 H), 2.79-2.65 (m, 3.4 H), 2.60 (s, 1 H), 2.37-2.36 (m, 1 H), 2.05-1.95 (m, 2 H), 1.90-1.80 (m, 1 H), 1.55-1.52 (m, 6 H).

Provenance & Evidence