Diisopropylethylamine → N-(3-{2-[4-(2-methyl-5-quinazolinyl)-1-piperazinyl]ethyl}phenyl)methanesulfonamide

HRID 1179626

Reaktionsgleichung

Reaktionsgleichung von HRID 1179626
[CH3:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:3]=1.CS(O[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:26]=1)(=O)=O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:23][CH2:24][C:25]3[CH:26]=[C:27]([NH:31][S:32]([CH3:35])(=[O:33])=[O:34])[CH:28]=[CH:29][CH:30]=3)[CH2:14][CH2:13]2)[N:3]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 57444358HCID 57444358, VerbindungHCID 574443592-{3-[(Methylsulfonyl)amino]phenyl}ethyl methanesulfonate

Produkt 1

HCID 57444357N-(3-{2-[4-(2-methyl-5-quinazolinyl)-1-piperazinyl]ethyl}phenyl)methanesulfonamideAusbeute 37,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-methyl-5-(1-piperazinyl)quinazoline (50 mg), 2-{3-[(methylsulfonyl)amino]phenyl}ethyl methanesulfonate (65 mg), diisopropylethylamine (192 μL) and DMF (0.5 mL) was heated to 100° C. in a sealed tube and stirred for 24 hours. The mixture was cooled to room temperature and partitioned between aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed (water, brine), dried (sodium sulfate) and concentrated in vacuo. The residue was purified by column chromatography [SiO2; DCM-MeOH: (100:0)→(95:5)] to give the title compound as a beige foam (35 mg).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between aqueous ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed (water, brine)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography [SiO2; DCM-MeOH: (100:0)→(95:5)]

Quellen und Nachweise

ORD-Eintrag
ord-e9d2ec95763d4c97b00098cb96be5227
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279481B2

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