Isopropylamine → HCID 118036662, compound

Temperature

50 °C

A mixture of isopropylamine (1.83 ml, 21.3 mmol), 6-amino-4-fluoronicotinonitrile (intermediate 21, 972 mg, 7.09 mmol) and diisopropylethylamine (3.71 ml, 21.3 mmol) in DMA (17 ml) was heated at 50° C. in a septum sealed reaction vessel for 48 h. The reaction mixture was then cooled, evaporated and purified by normal phase chromatography using an 40 g RediSep® column, eluting with a gradient from DCM to 10% MeOH in DCM. Product containing fractions were combined and evaporated. The residue was partitioned between DCM and 10% aqueous citric acid solution, the aqueous layer washed 2× with DCM, basified with NaHCO3, extracted with DCM (4×), the combined organic extracts from the basic extraction dried over Na2SO4 and evaporated to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.89 (s, 1H), 6.31 (s, br, 2H), 5.71 (d, br, 1H), 5.58 (s, 1H), 3.61-3.49 (m, 1H), 1.14 (d, 6H).

1. customsealed
2. customreaction vessel for 48 h
3. temperatureThe reaction mixture was then cooled
4. customevaporated
5. custompurified by normal phase chromatography
6. washeluting with a gradient from DCM to 10% MeOH in DCM
7. additionProduct containing fractions
8. customevaporated
9. customThe residue was partitioned between DCM and 10% aqueous citric acid solution
10. washthe aqueous layer washed 2× with DCM
11. extractionextracted with DCM (4×)
12. extractionthe combined organic extracts from the basic extraction
13. dry with materialdried over Na2SO4
14. customevaporated

ORD record

ord-7d068b4210b648a3bdea506e3fdecda3

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266883B2