Diisopropylethylamine → HCID 58447638, compound

Participants

Reaction Steps

A mixture of 2-(6-thiomorpholinopyridin-3-yl)acetic acid 219-4 (92 mg, 0.39 mmol), 6-(3-fluorophenyl)pyridin-3-amine 219-1 (73 mg, 0.39 mmol), HATU (162 mg, 0.43 mmol) and DIEA (104 μl, 0.6 mmol) in DMF (1.0 ml) was stirred at room temperature overnight. Then it was redistributed between water (30 ml) and ethyl acetate (40 ml). The organic phase was dried over Na2SO4 and concentrated by rotary evaporation. Silica gel column chromatography (with ethyl acetate/hexanes from 1:10 to 2:1 as eluent) gave N-(6-(3-fluorophenyl)pyridin-3-yl)-2-(6-thiomorpholinopyridin-3-yl)acetamide 219-5 as solid. Step 7. N-(6-(3-fluorophenyl)pyridin-3-yl)-2-(6-thiomorpholinopyridin-3-yl)acetamide 219-5 (114 mg, 0.28 mmol) was treated with mCPBA in DCM (2 ml) at 0° C. The mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (30 mL), washed with 5% Na2CO3 solution, dried over Na2SO4 and concentrated by rotary evaporation. The residue was subjected to reverse phase HPLC purification and gave N-(6-(3-fluorophenyl)pyridin-3-yl)-2-(S,S-dioxo-6-thiomorpholinopyridin-3-yl)acetamide 219 as solid. MS m/z 396.3 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 10.53 (s, 1 H), 8.82 (d, 1 H), 8.16 (dd, 1 H), 8.11 (d, 1 H), 7.99 (d, 1 H), 7.92-7.80 (m, 2 H), 7.60 (dd, 1 H), 7.50 (m, 1 H), 7.22 (m, 1 H), 7.02 (d, 1 H), 4.06-4.01 (m, 4 H), 3.61 (s, 2 H), 3.10-3.05 (m, 4 H).

Provenance & Evidence