Diisopropylethylamine → HCID 67111735, compound

Participants

Reaction Steps

Glycine ethyl ester hydrochloride (224 mg, 1.602 mmol) was dissolved in MeOH (4.0 mL) and chloroform (4.0 mL) before diisopropylethylamine (279 μL, 1.602 mmol) was added and stirred at ambient temperature for 15 min. 3-Fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (300 mg, 0.801 mmol) and sodium triacetoxyhydroborate (340 mg, 1.602 mmol) were then added and stirred at ambient temperature for 24 h. The reaction mixture was diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 1 time with 50 mL of ammonium chloride (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give ethyl 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo-[5,4-b]pyridin-2-yl)benzylamino)acetate after flash chromatography. MS (ESI) m/z: Calculated: 461.2; Observed: 461.9 (M++H).

Provenance & Evidence