Sodium hydride → HCID 21027721, compound

Imidazole-4-carboxylic acid methyl ester (756 mg, 6 mmol) was added slowly to a stirred suspension of sodium hydride (248 mg, 6.2 mmol) in tetrahydrofuran (10 mL) under nitrogen. The reaction mixture was stirred at room temperature for 30 minutes before being treated dropwise with 2-(2-bromoethoxy)-tetrahydro-2H-pyran (1.34 g, 6.4 mmol) and lithium iodide (40 mg, 0.3 mmol). The reaction mixture was allowed to stir at room temperature under nitrogen for 72 hours and then at reflux for 24 hours. The reaction mixture was cooled and diluted with a mixture of ethyl acetate:water 1:1 (300 mL). The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The organics were combined, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol 100:0 to 98:2 to 96:4 to yield the title product.

1. stirringto stir at room temperature under nitrogen for 72 hours
2. temperatureat reflux for 24 hours
3. temperatureThe reaction mixture was cooled
4. customThe aqueous layer was separated
5. extractionextracted with ethyl acetate (2×50 mL)
6. dry with materialdried over magnesium sulphate
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol 100:0 to 98:2 to 96:4

ORD record

ord-45af44506fdd42588b2c455d4aceb7fb

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07056934B2