Triethylamine → (2-Methyl-4-(4-phenylphthalazin-1-yl)piperazin-1-yl)(thiophen-2-yl)methanone

HRID 1689941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689941
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:10][N:9]=2)[CH2:3]1.C(N(CC)CC)C.[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[C:36](Cl)=[O:37]>ClCCl.C(OCC)(=O)C>[CH3:1][CH:2]1[CH2:3][N:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:10][N:9]=2)[CH2:5][CH2:6][N:7]1[C:36]([C:32]1[S:31][CH:35]=[CH:34][CH:33]=1)=[O:37]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 575814991-(3-Methylpiperazin-1-yl)-4-phenylphthalazine

Produkt 1

HCID 25152617(2-Methyl-4-(4-phenylphthalazin-1-yl)piperazin-1-yl)(thiophen-2-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-methylpiperazin-1-yl)-4-phenylphthalazine BSL-2 (200 mg, 0.58 mmol) in 10 mL dichloromethane was added triethylamine (0.23 mL, 1.6 mmol, 3 eq) and thiophene-2-carbonyl chloride (0.095 mL, 0.88 mmol, 1.5 eq). After 2 h, the reaction was diluted with ethyl acetate and washed with sat. NaHCO3, water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by column chromatography afforded (2-methyl-4-(4-phenylphthalazin-1-yl)piperazin-1-yl)(thiophen-2-yl)methanone, 1. MS (M+H)+=415.1.

Aufarbeitung

  1. washwashed with sat. NaHCO3, water, and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-20ec7b1da29048a69e91a5bf087dc141
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153633B2

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