Toluene → HCID 42606681, compound

Participants

Reaction Steps

To a solution of ethyl 2-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-4-methyl-1,3-thiazole-5-carboxylate (Example 2) (0.1 g, 0.22 mmol) in THF was added a 1M solution of DIBAL-H in toluene (2.76 mL, 6 eq) and the reaction was stirred to room temperature for 27 hours. Ether was added followed by solid NH4Cl. After 30 min, water was added and the mixture was filtered. The aqueous phase was extracted with ether, dried over sodium sulphate and evaporated. After purification by flash chromatography, eluting with DCM/MeOH 95/5, and crystallisation from acetonitrile, the title compound was obtained as a white solid (3 mg, 3%). HRMS calculated for C16H15Cl2N5O2S (M+H)+412.0402, found: 412.0409, Rt: 2.65 min. MP: 161.8° C.

Provenance & Evidence