2-Amino-2-methyl-1-propanol → HCID 90011361, compound

Participants

Reaction Steps

Step-1: 1-(5-Bromopyridin-2-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide: To (0° C.) cooled solution of 1-(5-bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acid (500 mg, 1.48 mmol), in DCM (20 mL) was added oxalyl chloride (391 μL, 4.46 mmol) followed by catalytic amount of DMF. The resulting mixture was stirred at room temperature for 3 h. The solvent and excess of oxalyl chloride was then removed under vacuum and the resulting residue was dissloved in DCM (10 mL). A solution of 2-amino-2-methylpropan-1-ol (0.35 mL, 3.72 mmol) in DCM (5 mL) was then added to the above solution drop-wise at 0° C. and the resulting mixture was warmed to room temperature and then continued stirring at the same temperature for 18 h. Water (10 mL) was added to the above reaction followed by DCM (20 mL). The layers were separated and the aqueous layer was extracted with DCM (3×10 mL). The combined organic layers were washed with bine (10 mL), dried (anhydrous Na2SO4) and filtered. The filtrate was rotary evaporated and the crude product was purified by flash column chromatography to afford 600 mg (99%) of the title compound as white solid. 1HNMR (400 MHz, CDCl3) δ 8.61 (d, J=2.0 Hz, 1H), 8.04 (dd, J=2.0 & 8.0 Hz, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.37 (s, 1H), 6.96 (s, 1H, D2O exchangeable), 3.73 (s, 2H), 1.44 (s, 6H) ; ESI-MS (m/z) 407, 409 [(MH)+, Br79,81].

Provenance & Evidence