Sodium Hydroxide → HCID 178433160, compound

Participants

Reaction Steps

800 mg (2.40 mmol) of trans-2-chloro-N-(4-formyl-cyclohexyl)-5-trifluoromethyl-benzamide (Example 1 Step 3) and 274 mg (2.40 mmol) of 5-methylthiazol-2-amine are placed in a flask with 40 mL of DCM. 191 mg (3.60 mmol) of sodium triacetoxyborohydride is added and the RM is stirred at room temperature overnight 1N sodium hydroxide (2 mL) is added and the mixture is stirred at RT for 10 min. The RM is partitioned between DCM and water. The organic phase is washed with water and brine, dried over MgSO4, filtered and the solvent is removed in vacuo. The product is purified by ISCO Combiflash Rf (80 g Si, iso-hexane→EtOAc, default setting). The product crystallized out on the column and had to be eluted with EtOAc (10% MeOH). The solvent is removed in vacuo and the product is crystallized from EtOAc, filtered and dried for 4 days under vacuum @50° C.

Provenance & Evidence