1,2-Dichloroethane → HCID 89813286, Verbindung

Temperatur

0 °C

To a solution of 4-(4-chlorophenyl)thiazole-2-carboxylic acid (prepared according to the procedure given in US 2007/32531, 1.00 g, 4.17 mmol) in DMF (10 ml) was added HOST (0.96 g, 6.26 mmol) at room temperature, followed by the addition of piperidine (0.42 g, 5.01 mmol). The reaction mixture was cooled to 0° C. and to this were added EDC (1.20 g, 6.26 mmol) and triethylamine (2.11 g, 2.91 ml, 20.86 mmol). The reaction mixture was stirred at room temperature for 15 hr and the progress of reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure. The residue so obtained was taken in ethyl acetate (50 ml) and washed with saturated sodium bicarbonate solution (1×40 ml), brine (1×20 ml) and organic layers separated were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get a crude product. The crude product was purified by column chromatography over silica gel (100-200 mesh) using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (0.41 g, 32.4%). MS: m/z 308 (M+1).

1. additionwas added HOST (0.96 g, 6.26 mmol) at room temperature
2. customthe progress of reaction
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. customThe residue so obtained
5. washwashed with saturated sodium bicarbonate solution (1×40 ml), brine (1×20 ml) and organic layers
6. customseparated
7. dry with materialwere dried over anhydrous sodium sulphate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto get a crude product
11. customThe crude product was purified by column chromatography over silica gel (100-200 mesh)

ORD-Eintrag

ord-57bb51c4eadf4fc49d345108a092d48b

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09388196B2