Diisopropylethylamine → N-(1-(2,2-dimethoxyethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

Participants

Reaction Steps

To a solution of 5-(m-tolyl)oxazole-4-carboxylic acid (5.34 g, 26.28 mmol) in DCM (135 mL), TBTU (12.66 g, 39.42 mmol) and DIPEA (13.50 mL, 78.84 mmol) was added. After stirring for 30 min at rt, 1-(3,3-dimethoxypropyl)-1H-pyrazol-4-amine (4.50 g, 26.29 mmol) dissolved in DCM (15 mL) and DMF (2 mL) was added to the reaction mixture and stirred at rt for 1 h, then the reaction mixture was diluted with DCM and water, the org. layer was separated and the aq. layer extracted with DCM (1×). The combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification by FC (EtOAc/hept 7:3) yielded N-(1-(2,2-dimethoxyethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide as a pale yellow solid. LC-MS conditions A: tR=0.82 min, [M+H]+=357.06.

Provenance & Evidence