Hydrochloric Acid → HCID 86638721, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-(3,3-difluorocyclopentyl)-cyclopropyl)thiazolo[5,4-b]pyridine was treated with 5 mL THF and 5N HCl was sealed and heated to 70° C. for 1 h. The reaction mixture was cooled, quenched with ice and 10 N NaOH until basic, and diluted with water and DCM. The aq. Layer was extracted with DCM, and the combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil. The oil was adsorbed onto 5 g silica gel and dried, purified by silica gel chromatography, 0-40% EA/hexanes, to give (rac)-4-(5-(1-(3,3-difluorocyclopentyl)-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde as a solid. MS (ESI) m/z: Calculated: 402.1; Observed: 403.0 (M++1).

Provenance & Evidence