Acetyl chloride → HCID 11951617, compound

Participants

Reaction Conditions

Reaction Steps

[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluorophenyl)methanone (0.10 g, 0.31 mmol) (Example 6) was dissolved in a mixture of tetrahydrofuran (20 mL), chloroform (6 mL), and pyridine and cooled to −10° C. This was treated with acetyl chloride (0.032 g, 43 mmol) and stirred for 0.5 hr. at room temperature. This was diluted with cold methylene chloride (100 mL) and washed with 10% Na2CO3(aq) (2×). After drying (Na2SO4) and solvent removal, the residue was precipitated from a mixture of tetrahydrofuran and hexane to give 35 mg (30% yield) of 1-[4-[4-amino-5-(3-fluorobenzoyl)thiazol-2-ylamino]piperidin-1-yl]ethanone. 1H NMR (DMSO−d6, 300 MHz) δ1.28 (m, 1H, CH), 1.41 (m, 1H, CH) 1.92 (m, 2H, CH2), 2.75 (t, 1H, NCH), 3.14 (t, H, NCH), 3.32 (s, 3H, COCH3), 3.6-4.0 (broad, 1H, CH), 3.77 (d, 1H, NCH), 4.22 (d, 1H, NCH), 7.31 (t, 1H, Aromatic), 7.38 (d, 1H, Aromatic), 7.48 (t, 1H, Aromatic), 7.51 (q, 1H, Aromatic), 8.01 (brd, 1H, NH), 8.48 (brd, 1H, NH), 8.72 (brd, 1H, NH). HRMS: (M+H)+: observed: 363.1288; calcd for 363.1286.

Provenance & Evidence