L-Methioninol → N-[[1-[[[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninol

HRID 448781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448781
[NH2:1][C@H:2]([CH2:7][OH:8])[CH2:3][CH2:4][S:5][CH3:6].[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][C:30](=[O:32])[C:29]5([CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)[N:28]=4)=[CH:23][CH:22]=3)[N:20]=2)[CH2:12][CH2:11]1>CN(C)C=O>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([NH:28][C:29]4([C:30]([NH:1][C@H:2]([CH2:7][OH:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:32])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]4)=[O:31])=[CH:25][CH:26]=3)[N:20]=2)[CH2:12][CH2:11]1

Komponenten

4

Edukt 2

HCID 2724404L-MethioninolHCID 576728032-[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Produkt 1

HCID 57672850N-[[1-[[[4-[2-(4-Methyl-1-piperazinyl)-4-thiazolyl]phenyl]carbonyl]amino]cyclohexyl]carbonyl]-L-methioninolAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

100 mg (0.74 mmol) of L-methioninol was added to a solution of 250 mg (0.68 mmol) of 2-[4-[2-(4-methyl-1-piperazinyl)-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one in 20 ml of dimethylformamide. After the mixture was stirred at 80° C. for 15 hours, the reaction solution was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, and diisopropyl ether was added to the residue to wash the crystal to obtain 319 mg (86%) of the title compound.

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was successively washed with water
  4. dry with materialby drying with anhydrous sodium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure, and diisopropyl ether
  6. additionwas added to the residue
  7. washto wash the crystal

Quellen und Nachweise

ORD-Eintrag
ord-fa3326ca2b774c608a65c4913075f958
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481725B2

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