4-[4-Amino-5-(3-fluorobenzoyl)thiazol-2-ylamino]piperidine-1-carboxylic acid tert-butyl ester → HCID 11951611, compound

Participants

Reaction Steps

4-[4-Amino-5-(3-fluorobenzoyl)thiazol-2-ylamino]piperidine-1-carboxylic acid tert-butyl ester (0.82 g, 1.95 mmol) (Example 3) was dissolved in a mixture of trifluoroacetic acid (16 mL) and methylene chloride (30 mL). After 1 hr, all solvent was removed and the residue dissolved in methylene chloride (300 mL). This was washed with 10% Na2CO3 (50 mL), dried (Na2SO4) and concentrated to give a semi solid. This was triturated with ethyl ether and filtered to give 450 mg (72% yield) of [4-amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluorophenyl)methanone. 1H NMR (DMSO−d6, 300 MHz) δ1.38 (m, 2H, CH2), 1.88 (m, 2H, CH2), 2.95 (m, 2H, CH2), 3.32 (brd, 2H, CH2), 3.6-4.0 (broad, 1H, CH), 3.78 (s, 3H, OCH3), 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), 8.70 (brd, 1H, NH). LR-MS-ES(±): Compatible with 320 MW.

Provenance & Evidence