2-(Dimethylamino)ethanol → HCID 136436926, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the title compound of Example 26 (200 mg, 0.35 mmol), potassium bis(trimethylsilyl)amide (352 mg, 1.76 mmol) and 2-dimethylaminoethanol (1.5 ml) was stirred at 90° C. for 18 hours, then allowed to cool. Water (5 ml) was added, the mixture extracted with ethyl acetate (3×5 ml) and the combined extracts dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using an elution gradient of dichloromethane: methanol (95:5 to 90:10), to give the title compound (147 mg, 68%) as an off-white foam. Found: C, 56.35; H, 6.37; N, 20.12. C29H39N9O4S; 0.50 H2O requires C, 56.29; H, 6.52; N, 20.37%. δ (CDCl3): 0.94 (3H,t), 1.04 (3H,t), 1.72 (2H,m), 2.43 (8H,m), 2.56 (4H,m), 2.74 (2H,t), 2.95 (2H,t), 3.15 (4H,m), 4.80 (2H,t), 5.67 (2H,s), 7.07 (1H,d), 7.21 (1H,m), 7.61 (1H,m), 8.56 (1H,d), 8.62 (1H,s), 8.75 (1H,s), 12.23 (1H,s). LRMS: m/z 610 (M+1)+.

Provenance & Evidence