Diisopropylethylamine → Benzimidazole

General working instructions 14 (GWI-14): To a solution of (ACI) (1.0 eq.) in THF was added diisopropyl ethylamine (4.0 eq.) at 0° C. followed by HATU (1.5 eq.). The resultant reaction mixture was allowed to stir at room temperature for 15 min. It was again cooled to 0° C. and a solution of the amine (1.3 eq.) in THF-DMF (3:1) was added. The reaction mixture was allowed to stir at room temperature for 16 h. The mixture was then diluted with methylene chloride, washed with saturated ammonium chloride solution, saturated sodium bicarbonate solution and finally with brine. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give the crude product which was purified by neutral alumina column chromatography to obtain desired product.

1. customThe resultant reaction mixture
2. temperatureIt was again cooled to 0° C.
3. stirringto stir at room temperature for 16 h
4. washwashed with saturated ammonium chloride solution, saturated sodium bicarbonate solution and finally with brine
5. dry with materialThe organic layer was dried over sodium sulfate
6. customevaporated to dryness under reduced pressure
7. customto give the crude product which
8. customwas purified by neutral alumina column chromatography

ORD record

ord-cc2d3e3adbcb4529a4fb797cd240bd93

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232288B2