Water → 1-(4-Chloroquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-one

HRID 1432988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432988
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][C@@H:16](C)[C:15]3=[O:21])=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:29][C:30]1[CH:31]=[CH:32][C:33]2[CH:37]=[C:36]([S:38](Cl)(=[O:40])=[O:39])[S:35][C:34]=2[CH:42]=1.O>C(#N)C>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([S:38]([C:36]4[S:35][C:34]5[CH:42]=[C:30]([Cl:29])[CH:31]=[CH:32][C:33]=5[CH:37]=4)(=[O:40])=[O:39])[CH2:16][C:15]3=[O:21])=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 69024355HCID 69024355, Verbindung

Produkt 1

HCID 179852311-(4-Chloroquinolin-7-ylmethyl)-4-(6-chlorobenzo[b]thiophen-2-sulfonyl)-piperazin-2-oneAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

1-(4-chloroquinolin-7-ylmethyl)-3-(S)-methylpiperazin-2-one hydrochloride (0.49 g, 1.4 mmol), EXAMPLE 89, is treated with acetonitrile (20 mL), triethyl amine (1.2 ml, 8.4 mmol) and a solution of 6-chlorobenzo[b]thiophen-2-sulfonyl chloride (0.41 g, 1.54 mmol), EXAMPLE 1, in acetonitrile (10 mL) at 0° C. After 2 h the solution is poured into water and extracted with ethyl acetate. The organic layer is washed with water, dried over sodium sulfate and concentrated to yielded the title compound (0.45 g, 0.95 mmol). MS m/z: 506, [M+1]+; 1H NMR (CD3OD, 300 MHz) δ8.8 (d, 1H), 8.15 (d, 1H), 7.9 (d, 2H), 7.85 (s, 1H), 7.4-7.5 (m, 2H), 6.8 (s, 1H), 4.8 (s, 2H), 4.0 (s, 2H), 3.4-3.45 (m, 4H).

Aufarbeitung

  1. customat 0° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-46a88451f2434cc58eb5edafd9e70cf9
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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