Hydrochloric Acid → N-((1S,3R,4S)-3-ethyl-4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide

温度

80 °C

A mixture of N-((1S,3R,4S)-3-ethyl-4-(6-tosylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide (0.119 g, 0.214 mmol) and 1N aqueous NaOH (0.428 mL, 0.428 mmol) in 1,4-dioxane (2 mL) was heated at about 80° C. for about 40 min. Aqueous NaOH (1 N, 0.428 mL, 0.428 mmol) was added and the reaction mixture was heated at about 80° C. for about for 3.5 h. The reaction mixture was cooled to ambient temperature and concd under reduced pressure. The residue was dissolved in EtOAc (10 mL) and water (10 mL). The pH was adjusted to about 5 by the addition of 1 N aqueous HCl. The organic layer was separated, dried over anhydrous MgSO4, filtered and concd under reduced pressure. The residue was triturated with Et2O (5 mL) and the solvent was removed by pippette. The residue was dried under reduced pressure to give a bright yellow solid that was purified by chiral chromatography [Table 2, Method 39, Rt=16.6 min, or =negative) to give N-((1S,3R,4S)-3-ethyl-4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide (0.036 g, 45%): LC/MS (Table 1, Method a) Rt=1.71 min; MS m/z 374 (M+H)+.

1. temperaturethe reaction mixture was heated at about 80° C. for about for 3.5 h
2. temperatureThe reaction mixture was cooled to ambient temperature
3. customThe organic layer was separated
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. customThe residue was triturated with Et2O (5 mL)
7. customthe solvent was removed by pippette
8. customThe residue was dried under reduced pressure
9. customto give a bright yellow solid
10. customthat was purified by chiral chromatography [Table 2, Method 39, Rt=16.6 min, or =negative)

ORDレコード

ord-0bfeeba581f043f6aee985a1e20e2989

出典データセット

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08426411B2