Ammonium Chloride → HCID 10429705, compound

Participants

Reaction Conditions

Reaction Steps

Trimethyl aluminum (2M/toluene, 2.55 mL, 5.1 mmol) is added to a dry flask containing ammonium chloride (272.3 mg, 5.1 mmol). The solution is then allowed to stir for 30 min and is added to a dry flask containing compound 21 (100 mg, 0.26 mmol). The reaction is then heated to 80° C. for 4 hours and then cooled to room temperature. The reaction is then carefully quenched with 1 N HCl and extracted with EtOAc (×3). The combined organics are dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (20%→50% EtOAc/methylene chloride) provides 3-(4-Chloro-benzylsulfanyl)-5-(pyrimidin-2-ylamino)-isothiazole-4-carboxylic acid amide (16.2 mg, 17%) in addition to the starting material 21 (36.6 mg). 1H NMR (d6 DMSO): δ 11.61 (1H, br. s), 8.73 (2H, d, J=5.0 Hz), 7.43 (2H, d, J=8.4 Hz), 7.34 (2H, d, J=8.4 Hz), 7.15 (1H, dd, J=5.0, 5.0 Hz), 4.46 (2H, s). LRMS (M+): 378.1, (M−): 376.0.

Provenance & Evidence