Diisopropylethylamine → HCID 57989800, compound

Temperature

50 °C

A mixture of N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide (0.15 g, 0.28 mmol), 1-(2-aminoethyl)-2-pyrrolidinone (0.18 g, 0.83 mmol) and DIEA (0.10 ml, 0.56 mmol) in MeOH (0.5 ml) was heated at 50° C. for 2 h. LCMS analysis indicated that the reaction was proceeding very slowly, another equivalent amine and DIEA was added and the reaction was heated overnight. LCMS analysis indicated the reaction had still not progressed sufficiently so the reaction was heated overnight again. LCMS analysis indicated the reaction had progressed sufficiently so the reaction mixture was concentrated onto silica gel and purified by flash chromatography to afford a colourless foam. The product was dissolved in DCM and washed with HCl (10% Aq.) to remove some residual DIEA and the organics were dried over MgSO4, filtered and the filtrate was concentrated in vacuo to afford the title compound (0.12 g, 67% yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 10.77 (s, 1H), 8.07 (d, J=5.1 Hz, 1H), 7.22-7.65 (m, 7H), 3.21-3.45 (m, 6H), 2.11-2.22 (m, 2H), 1.82-1.93 (m, 2H), 1.41 (s, 9H). MS (ES+): 631 [M+H]+.

1. temperaturethe reaction was heated overnight
2. temperaturewas heated overnight again
3. concentrationwas concentrated onto silica gel
4. custompurified by flash chromatography
5. customto afford a colourless foam
6. washwashed with HCl (10% Aq.)
7. customto remove some residual DIEA
8. dry with materialthe organics were dried over MgSO4
9. filtrationfiltered
10. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-4821cc9eeba24bb99bcf99fef09b30cc

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415345B2