Ethylenediamine → HCID 67277766, compound

Temperature

110 °C

To a solution of 3-methyl-1-[(1S,2R)-2-methylcyclohexyl]-6-{[2-(trimethylsilyl)ethoxy]methyl}-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (40 mg) in water (2 mL) was added trifluoroacetic acid (2 mL) and the mixture was stirred 110° C. for 3 hours. The mixture was extracted with chloroform. The extract was washed with saturated aqueous sodium hydrogencarbonate and water, dried over MgSO4, filtrated and evaporated to give a white solid. The solid was dissolved with tetrahydrofuran (2 mL) and saturated potassium carbonate aqueous solution (2 mL) was added. The mixture was stirred for 1 hour. To the mixture was added 1,2-ethanediamine (0.5 mL) and the mixture was stirred for 1 hour. The mixture was extracted with chloroform. The extract was washed with water, dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 95:5) to give 3-methyl-1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (25 mg) as a white powder.

1. extractionThe mixture was extracted with chloroform
2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate and water
3. dry with materialdried over MgSO4
4. filtrationfiltrated
5. customevaporated
6. customto give a white solid
7. additionwas added
8. stirringThe mixture was stirred for 1 hour
9. stirringthe mixture was stirred for 1 hour
10. extractionThe mixture was extracted with chloroform
11. washThe extract was washed with water
12. dry with materialdried over MgSO4
13. filtrationfiltrated
14. customevaporated
15. customThe residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 95:5)

ORD record

ord-917ab3082dce4535bca4a62e10f67a96

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163767B2