Diisopropylethylamine → HCID 44227500, Verbindung

5-(1H-Pyrazol-4-yl)-thiophene-3-carboxylic acid (0.080 g, 0.41 mmol) was suspended in acetonitrile (2 mL) then DIPEA (0.158 mL, 0.90 mmol) and 1-(2,2,2-trifluoro-ethyl)-decahydro-quinoxaline (0.119 g, 0.54 mmol) were added followed by HATU (0.192 g, 0.50 mmol). The resulting mixture was stirred for about 24 hours and then further amounts of DIPEA (79 μL) and HATU (0.192 g) were added and stirring continued over the weekend. The mixture was evaporated and the residue was taken up in sodium hydroxide (1N) and stirred for 30 minutes. HCl (1 N, 2.5 mL) was added and the solution extracted with ethyl acetate (×3). The organics were dried over sodium sulfate, filtered and evaporated. The material was purified by HPLC, eluting with 5%-95% acetonitrile in water (0.1% formic acid) and the fractions containing the desired product were combined and freeze-dried to give the title compound as a white solid (0.020 g). LCMS m/z 399.17 [M+H]+ R.T.=10.05 min (Analytical Method 2).

1. stirringstirring
2. customThe mixture was evaporated
3. stirringstirred for 30 minutes
4. additionHCl (1 N, 2.5 mL) was added
5. extractionthe solution extracted with ethyl acetate (×3)
6. dry with materialThe organics were dried over sodium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe material was purified by HPLC
10. washeluting with 5%-95% acetonitrile in water (0.1% formic acid)
11. additionthe fractions containing the desired product
12. customfreeze-dried

ORD-Eintrag

ord-499526199e1c419d9b2a78b1f8d8ade2

Quelldatensatz

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08299063B2