Cyclopentanecarbonyl chloride → N-((3-(5-(3-methyl-1-oxo-1-(2,2,2-trifluoroethylamino)butan-2-ylamino)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methyl)cyclopentanecarboxamide

2-(5-(5-(aminomethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide 10-1c (30 mg, 0.071 mmol) was added to DMSO (0.5 ml) followed by the addition of diisopropylethylamine (0.031 ml, 0.178 mmol). Cyclopentanecarbonyl chloride (9.4 mg, 0.086 mmol) was added and the reaction stirred at room temperature for 3 hrs. The reaction was quenched by addition of methanol. The mixture was diluted with DMSO, filtered and purified by RP-HPLC (water:acetonitrile w/0.1% TFA, C-18, 15-50%). The pure fractions concentrated to remove acetonitrile and mixture neutralized with saturated sodium bicarbonate. The product was extracted with ethyl acetate (3×10 mL). The combined organics were then washed with brine, dried with sodium sulfate, filtered and concentrated to afford the product 10-1. LRMS (ESI) m/z 517.2 [(M+H)+; calcd for C26H31F3N6O2: 517.3

1. customThe reaction was quenched by addition of methanol
2. additionThe mixture was diluted with DMSO
3. filtrationfiltered
4. custompurified by RP-HPLC (water:acetonitrile w/0.1% TFA, C-18, 15-50%)
5. concentrationThe pure fractions concentrated
6. customto remove acetonitrile and mixture
7. extractionThe product was extracted with ethyl acetate (3×10 mL)
8. washThe combined organics were then washed with brine
9. dry with materialdried with sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-a1dd87cd7285494bb38402bf7eb832f1

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096598B2