tert-butyl N-(3-bromopropyl)carbamate → Ethyl 8-anilino-2-{3-[(tert-butoxycarbonyl)amino]propyl}-4,5-dihydro-2H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 44624

Reaktionsgleichung

Reaktionsgleichung von HRID 44624
[NH:1]([C:8]1[N:17]=[CH:16][C:15]2[CH2:14][CH2:13][C:12]3[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:19][NH:20][C:11]=3[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Li+].[C:32]([O:36][C:37]([NH:39][CH2:40][CH2:41][CH2:42]Br)=[O:38])([CH3:35])([CH3:34])[CH3:33]>CN(C)C=O.O1CCCC1>[NH:1]([C:8]1[N:17]=[CH:16][C:15]2[CH2:14][CH2:13][C:12]3=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:19]([CH2:42][CH2:41][CH2:40][NH:39][C:37]([O:36][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:38])[N:20]=[C:11]3[C:10]=2[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 178470474HCID 178470474, Verbindung

Produkt 1

HCID 68931717Ethyl 8-anilino-2-{3-[(tert-butoxycarbonyl)amino]propyl}-4,5-dihydro-2H-pyrazolo[4,3-h]quinazoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

500 mg of ethyl 8-anilino-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (1.5 mmol) were dissolved in 10 mL of dry dimethylformamide and 1.63 mL of 1M lithium tert-butoxide in tetrahydrofuran were added to the cooled solution. After 30 minutes under stirring at 0° C. a solution of 432 mg of tert-butoxycarbonylaminopropyl bromide in 8 mL of dry tetrahydrofuran were added dropwise. After a night at room temperature the mixture was poured into a solution of NaH2PO4 and extracted with dichloromethane. The organic layer was then dried over Na2SO4 and the solvent evaporated, giving an oil that was treated according to the following step 7, without any further purification.

Aufarbeitung

  1. additionwere added dropwise
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was then dried over Na2SO4
  4. customthe solvent evaporated
  5. customgiving an oil that
  6. additionwas treated
  7. customaccording to the following step 7, without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-c9881102c10b46b195f426b54d3cf480
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541429B2

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