Carbon Tetrachloride → HCID 178433940, compound

Participants

Reaction Conditions

Reaction Steps

PS-Triphenylphosphine resin (Biotage, catalog No. 800380, 2.28 mmol/g, 0.167 g, 0.38 mmol)triethylamine (0.132 mL, 0.95 mmol), and CCl4 (40 μL, 0.38 mmol) were added to a suspension of (S)—N′-(1-iminoethyl)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (40 mg, 0.095 mmol) in dichloromethane (3 mL) and MeCN (3 mL), and the reaction mixture was heated to 50° C. for 2 hours. After cooling to ambient temperature, the mixture was treated with EtOAc, washed with water, dried over MgSO4, concentrated under reduced pressure. The crude was purified by silica gel flash column chromatography (4% MeOH in dichloromethane) to afford 7 mg (18%) of (S)-4-isopropyl-3-(3-(4-(5-methyl-4H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one. 1H NMR (400 MHz, CD3OD/CDCl3) δ 8.70 (d, 1H), 8.48 (s, 1H), 8.13 (m, 2H), 8.05 (m, 3H), 5.05 (m, 1H), 4.50 (m, 2H), 2.92 (m, 1H), 2.52 (s, 3H), 1.12 (d, 3H), 0.96 (d, 3H); LCMS (APCI+) m/z 404.3 [M+H]+.

Provenance & Evidence