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Hydrochloric Acid → N-{2,2-Dimethyl-6-[2-methyl-6-oxo-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-4-propylpyrimidin-1(6H)-yl]-3,4-dihydro-2H-chromen-4-yl}acetamide

HRID 1673855
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1673855
O[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[C:17](=[O:18])[C:16]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:32]5[NH:36][C:35](=[O:37])[O:34][N:33]=5)=[CH:22][CH:21]=4)=[C:15]([CH2:38][CH2:39][CH3:40])[N:14]=[C:13]3[CH3:41])[CH:10]=2)[O:5][C:4]([CH3:43])([CH3:42])[CH2:3]1.Cl>C(#N)C.C(OCC)(=O)C>[CH3:42][C:4]1([CH3:43])[CH2:3][CH:2]([NH:12][C:17](=[O:18])[CH3:16])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[C:17](=[O:18])[C:16]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:32]5[NH:36][C:35](=[O:37])[O:34][N:33]=5)=[CH:22][CH:21]=4)=[C:15]([CH2:38][CH2:39][CH3:40])[N:14]=[C:13]3[CH3:41])[CH:10]=2)[O:5]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 1359558823-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-2-methyl-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one

Produkt 1

HCID 136026967N-{2,2-Dimethyl-6-[2-methyl-6-oxo-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-4-propylpyrimidin-1(6H)-yl]-3,4-dihydro-2H-chromen-4-yl}acetamideAusbeute 153,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342
Acetonitrile
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-(4-Hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-2-methyl-5-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one (1.0 g) was dissolved in acetonitrile (10 mL), and concentrated hydrochloric acid (1.0 mL) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (0.82 g, 76%) as a colorless solid.

Aufarbeitung

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fb48a1b793aa4042aa01e5bd27e71ce4
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07998968B2

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