Dimethylformamide → HCID 15295337, compound

Participants

Reaction Conditions

Reaction Steps

The product from step C Example 1 (2.83 g, 10.07 mmol) was dissolved in DMF (40 mL). Sodium hydride (1.2 g, 30.21 mmol of a 60% suspension in mineral oil) was added slowly at room temperature. The mixture was stirred for 15 min and then chloroethylmorpholine hydrochloride salt (3.74 g, 20.14 mmol) was added. The mixture was warmed to 70° C. and stirred for 1h. DMF was evaporated under high vacuum. The residue obtained was diluted with 1N-HCl (50 mL) and washed with ethyl acetate (2×50 mL). The aqueous layer was neutralized with aqueous solution bicarbonate and extracted with ethyl acetate (3×50 mL). The combined ethyl acetate fractions were dried over MgSO4 and evaporated to provide a solid, repeated recrystallization from ethyl acetate-hexane yielded 1.35 g, (71%). mp: 160°-162° C. 1H NMR (DMSO-d6): δ: 2.38 (3H, s, CH3); 2.50 (4H, m, 2CH2N); 2.64 (2H, t, CH2); 3.50 (4H, m, 2CH2O); 4.01 (2H, t, CH2); 7.94 (1H, 1s, CH); 8.22 (2H, s, NH2 exchangeable). Analysis calculated for C12H18N4O5S3 -0.15 Ethyl acetate: C, 37.12; H, 4.74; N, 13.74. Found: C, 37.10; H, 4.79; N, 13.90.

Provenance & Evidence