Tetrahydrofuran → HCID 25211284, compound

Participants

Reaction Steps

Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 3,3-difluoroazetidine hydrochloride by the method described in Example 2 Method B reversing the order of addition such that solid acid chloride was added to a THF solution of triethylamine (containing and additional 1.1 eq to neutralize the azetadinyl hydrochloride salt) and azetidine derivative. The reaction mixture was evaporated to a solid, triturated and filtered with the aid of water, then washed with a 1 N aqueous hydrochloric acid solution followed by water. The solid was air dried and then chromatographed on silica gel with EtOAc/hexanes (25 then 50%) as eluant to afford product as a colorless solid (43 mg, 49%). 1H NMR (CDCl3) 2.37 (s, 3H), 4.68 (br, 4H), 4.19 (br, 2H), 7.53 (s, 2H). 19F NMR −100.6, −63.1. LC/MS 6.42 min, [M+1]+ 353.

Provenance & Evidence