Ethanolamine → 8-anilino-N-(2-hydroxyethyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 875128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875128
[NH:1]([C:8]1[N:17]=[CH:16][C:15]2[CH2:14][CH2:13][C:12]3[C:18]([C:22](OCC)=[O:23])=[N:19][N:20]([CH3:21])[C:11]=3[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([CH2:29][NH2:30])[OH:28]>CO.CN(C)C=O>[NH:1]([C:8]1[N:17]=[CH:16][C:15]2[CH2:14][CH2:13][C:12]3[C:18]([C:22]([NH:30][CH2:29][CH2:27][OH:28])=[O:23])=[N:19][N:20]([CH3:21])[C:11]=3[C:10]=2[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 700EthanolamineHCID 44232942HCID 44232942, Verbindung

Produkt 1

HCID 442363548-anilino-N-(2-hydroxyethyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a suspension of 0.30 g (0.86 mmol) of ethyl 8-anilino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate in a mixture of 10 mL of methanol and 10 mL of dimethylformamide, 5 mL of ethanolamine were added. The mixture was heated in a close bottle under stirring at 65° C. After 5 hours the solvent was removed, the residue redissolved with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and evaporated. The residue was triturated with diethyl ether and the product collected by filtration (60% yield).

Aufarbeitung

  1. additionwere added
  2. temperatureThe mixture was heated in a close bottle
  3. customAfter 5 hours the solvent was removed
  4. dissolutionthe residue redissolved with dichloromethane
  5. washwashed with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customevaporated
  8. customThe residue was triturated with diethyl ether
  9. filtrationthe product collected by filtration (60% yield)

Quellen und Nachweise

ORD-Eintrag
ord-200e0ea9a60a4e61a93b9613967b9af0
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981089B2

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