Dimethylamine → HCID 66928436, 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-hydroxymethyl-phenyl)-oxazole-4-carboxylic acid [1-(5-acetyl-furan-2-ylmethyl)-1H-pyrazol-3-yl]-amide (75 mg, 0.19 mmol) in CH2Cl2 (2.0 mL) was treated with DIPEA (0.05 mL, 0.28 mmol) followed by methanesulfonyl chloride (0.02 mL, 0.22 mmol). The reaction mixture was stirred for at rt 2.5 h before dimethylamine (0.9 mL of a 2N solution in THF, 1.8 mmol) was added and the reaction mixture was further stirred at rt for 8 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 FC (93:7 CH2Cl2-MeOH) gave the title compound as a pale yellow oil. TLC: rf (93:7 CH2Cl2-MeOH)=0.27. LC-MS-conditions 02: tR=0.74 min; [M+H]+=434.14.

Provenance & Evidence