Ethanol → HCID 10899819, compound

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (186 μL, 2.4 mmol) was added dropwise to a cooled (0° C.) CH2Cl2 solution (8 mL) containing 14b (362 mg, 2.0 mmol) and triethylamine (334 μL, 2.4 mmol) under Ar, and then the solution was stirred at 0-5° C. (1 h). CH2Cl2 (10 mL) was added to the reaction and the organic phase was successively washed with a saturated aqueous NaHCO3 solution (10 mL) and brine (2×10 mL), dried (Na2SO4), filtered and evaporated to give mesylate 14d (508 mg, 98%). Compound 14d was combined with a 2 M dimethylamine THF solution (10 mL, 20 mmol) and triethylamine (279 μL, 2.0 mmol) in EtOH (15 mL) and heated at 80° C. (15 h). The reaction solution was concentrated in vacuo and the residue taken up in CH2Cl2 (10 mL). The organic solution was washed with H2O (2×10 mL) and brine (2×10 mL), dried (Na2SO4), filtered and evaporated. The crude product was purified by PTLC (EtOAc) to give 14e (342 mg, 82%) as a yellow oil: Rf 0.17 (EtOAc/hexanes=3/1); IR (neat) 2976, 2821, 2776, 1723, 1599, 1459, 1376, 1282, 1117 cm−1; 1H NMR (CDCl3) δ 1.41 (t, J=7.2 Hz, 3H), 2.31 (s, 6H), 3.65 (s, 2H), 4.41 (q, J=7.2 Hz, 2H), 7.51 (d, J=7.8 Hz, 1H), 8.27 (dd, J=2.1, 7.8 Hz, 1H), 9.16 (d, J=2.1 Hz, 1H); 13C NMR (CDCl3) 14.2, 45.5 (2C), 61.2, 65.4, 122.4, 124.7, 137.3, 150.3, 163.5, 165.2 ppm; MS (+CI) 209 [M+1]+; Mr (+CI) 209.129 93 [M+1]+ (calcd for C11H17N2O2 209.129 00).

Provenance & Evidence