Dimethylamine → HCID 66928123, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-[3-(2-hydroxy-ethyl)-phenyl]-oxazole-4-carboxylic acid [1-(5-acetyl-furan-2-ylmethyl)-1H-pyrazol-3-yl]-amide (51 mg, 0.12 mmol) in CH2Cl2 (1.0 mL) was treated with DIPEA (0.03 mL, 0.18 mmol) followed by methanesulfonyl chloride (0.01 mL, 0.15 mmol). The reaction mixture was stirred at rt for 2.5 h before dimethylamine (0.9 mL of a 2N solution in THF, 1.8 mmol) was and the reaction mixture was further stirred at rt for 2 h. EA (10 mL) and sat. aq. NaHCO3 (10 mL) were added and the aqueous layer was extracted with EA (10 mL). The combined organic extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by HPLC gave the title compound as a pale yellow oil. LC-MS-conditions 02: tR=0.76 min; [M+H]+=448.25.

Provenance & Evidence