Tetrahydrofuran → HCID 58612182, compound

Participants

Reaction Steps

1M sodium hexamethyldisilazane in THF (1.42 mL, 1.42 mmol) was added to 5-chloro-benzo[1,3]dioxol-4-ylamine Compound 31a (as described in PCT Application WO03/008409) (221 mg, 1.29 mmol) in DMF at 0° C. and the mixture was stirred for 15 min. 7-chloro-2-methylsulfanyl-thiazolo[4,5-b]pyridine-6-carbonitrile Compound 1g (312 mg, 1.29 mmol) in DMF (1 mL) was added and the reaction mixture stirred for an additional 2 hr at ambient temperature. The mixture was then diluted with water and filtered through Celite 545 to form a plug. The celite plug was rinsed with EtOAc and the organic layer was isolated and washed with brine. The organic layer was dried over MgSO4, then filtered and evaporated onto silica gel. Isolation by flash chromatography (eluted with a 20 to 40% EtOAc/hexane gradient) gave 7-(5-chloro-benzo[1,3]dioxol-4-ylamino)-2-methylsulfanyl-thiazolo[4,5-b]pyridine-6-carbonitrile Compound 31b (30 mg) as a yellow oil. MS 377, 379 (MH+).

Provenance & Evidence