Reaktion #433824

Reaktionsgleichung

Compound 107

6-Methyl-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

1-(2-chloroethyl) pyrrolidine hydrochloride

potassium carbonate

→

pale yellow solids

Ausbeute 19.0%

6-Methyl-2-oxo-1-(2-pyrrolidin-1-yl-ethyl)-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

Ausbeute 19.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled
2. 2
   SonstigeThe solids formed
3. 3
   Filtrationwere filtered
4. 4
   Waschenwashed by water
5. 5
   Sonstigedried
6. 6
   SonstigeThe crude product was purified by flash chromatography
7. 7
   Wascheneluting with 0–10% methanol in ethylacetate gradient

Vorschrift

A solution of Compound 107 (1 g., 2.64 mmol), 1-(2-chloroethyl) pyrrolidine hydrochloride (2.24 g, 13.2 mmol), and potassium carbonate (3.64 g, 26.4 mmol) in DMF was heated overnight at 90° C. The solution was cooled and poured into ice water. The solids formed were filtered, washed by water, and dried. The crude product was purified by flash chromatography eluting with 0–10% methanol in ethylacetate gradient to yield 236 mg (19%) of pale yellow solids. M.P. 139–143° C. 1H NMR (DMSO-d6): δ 1.67 (m, 4H), 2.41 (s, 3H), 2.53 (m, 4H), 2.61 (m, 2H), 3.01 (m, 2H), 3.62 (m, 4H), 3.93 (m, 4H), 4.30 (m, 2H), 7.16 (dd, J=3.4, 4.8 Hz, 1H), 7.49 (m, 2H), 7.60 (m, 1H), 7.69 (s, 1H), 7.80 (d, J=5.2 Hz, 1H). EIMS m/z 476 (M+1). Anal. (C26H29N5O2S) C, H, N.

Quelle