(Diethylamino)sulfur trifluoride → HCID 11478611, compound

Participants

Reaction Conditions

Reaction Steps

Diethylaminosulfur trifluoride (7 mg, 0.044 mmol) was dissolved in dry CH2Cl2 and cooled with stirring under argon to −65° C. 3-Cyano-N-{(2S)-2-(3,4-dichlorophenyl)-4-[3-(4-oxopiperidin-1-yl)azetidin-1-yl]butyl}-N-methyl-1-naphthamide (Example 26; 40 mg, 0.071 mmol), which was dissolved in dry CH2Cl2 (0.5 mL), was then added. The external cooling was removed and the solution was stirred for 1 h. The reaction mixture was quenched by dropping it to a saturated solution of NaHCO3 aq. (6 mL). The organic solution was washed with water and then dried over MgSO4. The solvent was removed by evaporation and there was obtained 5 mg (12%) of the title compound as an oil. 1H NMR (500 MHz, CD3OD): 1.8-2.6 (cm, 7H), 2.6-3.3 (cm, 7H), 3.4-4.4 (cm, 9H), 5.0-5.3 (cm, 1H), 7.0-8.4 (cm, 7H), 8.4-8.6 (m, 1H), 8.9-9.0 (d, 1H); LCMS: m/z 567 (M+1)+.

Provenance & Evidence