Ammonia → (rac)-2-(4-(4-(Trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetamide

To a solution of (rac)-2-(4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetic acid hydrochloride (example 99) (34.6 mg, 0.093 mmol) in DMF (1 mL) was added N,N-triethylamine (31 μL, 0.22 mmol) and 1,1′-carbonyldiimidazole (18.0 mg, 0.11 mmol). The reaction was stirred at room temperature for 2 h, cooled (0°) and treated with aq. 25% ammonia solution (0.87 mL, 5.55 mmol) and evaporated after 30 min to give a 1:1 mixture of starting material and product. The residue was dissolved in CH2Cl2, dried (Na2SO4) and evaporated. The oil was again dissolved in DMF (1 mL) and N,N-triethylamine (15.5 μL, 0.11 mmol) and 1,1′-carbonyldiimidazole (18.0 mg, 0.11 mmol) were added. The reaction was stirred at room temperature for 2 h, cooled (0°) and treated with aq. 25% ammonia solution (0.87 mL, 5.55 mmol) and evaporated after 30 min at room temperature. The solution was evaporated, dried in vacuo and purified by flash chromatography (20 g SiO2, Telos-cartridge, 3% MeOH in CH2Cl2) to give the title compound (15 mg, 48%) as off-white solid. MS: 337.1 (M+H+).

1. temperaturecooled (0°)
2. customevaporated after 30 min
3. customto give
4. additiona 1:1 mixture of starting material and product
5. dry with materialdried (Na2SO4)
6. customevaporated
7. dissolutionThe oil was again dissolved in DMF (1 mL)
8. stirringThe reaction was stirred at room temperature for 2 h
9. temperaturecooled (0°)
10. customevaporated after 30 min at room temperature
11. customThe solution was evaporated
12. customdried in vacuo
13. custompurified by flash chromatography (20 g SiO2, Telos-cartridge, 3% MeOH in CH2Cl2)

ORD record

ord-bf5a543fd143474d8716047ae224bb3f

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187429B2