Ethanolamine → HCID 178521296, Verbindung

HRID 1620673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620673
Cl.[F:2][C:3]([F:34])([F:33])[C:4]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:5]=1[CH2:6][N:7]1[CH2:12][CH2:11][CH:10](/[CH:13]=[C:14]2/[C:15](NCC(O)=O)=[N:16][C:17](=[O:19])[S:18]/2)[CH2:9][CH2:8]1.C(N(C(C)C)C(C)C)C.[NH2:44][CH2:45][CH2:46][OH:47].F[P-](F)(F)(F)(F)F.C([C:57](=[N:63]O[C+](N(C)C)N1CCOCC1)[C:58](OCC)=[O:59])#N>CN(C=O)C.O>[F:34][C:3]([F:2])([F:33])[C:4]1[CH:28]=[C:27]([C:29]([F:31])([F:32])[F:30])[CH:26]=[CH:25][C:5]=1[CH2:6][N:7]1[CH2:12][CH2:11][CH:10](/[CH:13]=[C:14]2/[C:15]([NH:44][CH2:45][C:46]([NH:63][CH2:57][CH2:58][OH:59])=[O:47])=[N:16][C:17](=[O:19])[S:18]/2)[CH2:9][CH2:8]1

Komponenten

7

Edukt 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 178472143HCID 178472143, VerbindungHCID 178479765HCID 178479765, Verbindung

Produkt 1

HCID 178521296HCID 178521296, VerbindungAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-[(5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-2-oxo-2,5-dihydro-1,3-thiazol-4-yl]glycine hydrochloride (500 mg), N-ethyl-N-(1-methylethyl)propan-2-amine (0.49 mL) and 2-aminoethanol (172 mg) in DMF (5 mL) was added (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (403 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and the solid was recrystallized from diisopropyl ether/heptane to give the title compound (20 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  6. customthe solid was recrystallized from diisopropyl ether/heptane

Quellen und Nachweise

ORD-Eintrag
ord-d36d5fe395a14bceb153ec07ff768496
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772277B2

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