Acetonitrile → HCID 22221501, Verbindung

Temperatur

23 °C

The product from Example 29C and 2-chloromethyl-1H-benzoimidazole (0.88 mg) were combined and dissolved in DMF (7 mL)/triethylamine (1.5 mL). After stirring at 23° C. for 2 hours, the mixture was treated with acetonitrile (20 mL) and then allowed to stir for 24 hours. The reaction mixture was partitioned between CH2Cl2 (100 mL)/n-butanol (5 mL) and water (800 mL)/NH4OH (5 mL). The organic phase was separated, dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography to provide the title as a white solid (1.169 g (55%). mp 62-64° C.; Rf=0.26 (95:5 CH2Cl2:methanol:0.1% NH40H); MS 400 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 12.3 (bs, NH, 1H), 7.90 (d, 1H, J=3 Hz), 7.55 (m, 1H), 7.3-7.5 (m, 8H), 7.15 (m, 2H), 6.80 (d, 1H, J=9 Hz), 5.05 (s, 2H), 3.76 (s, 2H), 3.39 (t, 4H, J=5.1 Hz), 2.57 (t, 4H, J=5.1 Hz).

1. stirringto stir for 24 hours
2. customThe reaction mixture was partitioned between CH2Cl2 (100 mL)/n-butanol (5 mL) and water (800 mL)/NH4OH (5 mL)
3. customThe organic phase was separated
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationthe filtrate concentrated under reduced pressure
7. customThe residue was purified by flash chromatography
8. customto provide the title as a white solid (1.169 g (55%)

ORD-Eintrag

ord-150a97ec790b47f0b4dbe246269f4afe

Quelldatensatz

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06960589B2