4-Methylmorpholine → HCID 178448373, Verbindung

HRID 1068878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1068878
C[N:2]1[CH2:7][CH2:6][O:5]CC1.Cl[C:9]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10].[NH2:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[N:23][C:24]=2[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[NH:19][N:18]=1>C1COCC1>[CH2:12]([O:11][C:9]([NH:2][C@H:7]([C:6]([NH:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[N:23][C:24]=2[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[NH:19][N:18]=1)=[O:5])[CH:27]([CH3:32])[CH3:28])=[O:10])[C:13]1[CH:15]=[CH:20][CH:25]=[CH:24][CH:14]=1

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 178509242HCID 178509242, Verbindung

Produkt 1

HCID 178448373HCID 178448373, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Analogously to Example 5, 386 mg (1.53 mmol) of N-benzyloxycarbonyl-(D,L)valine in 3.2 ml of THF and 337 μl (3.07 mmol) of NMM are activated with 219 μl (1.68 mmol) of isobutyl chloroformate and then reacted with 400 mg (1.53 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6). The reaction mixture is concentrated by evaporation; ethyl acetate is added to the residue and the ethyl acetate suspension is washed with 2N HCl solution, sat. NaHCO3 solution and brine and finally the insoluble crude product is filtered off. Crystallization from a hot mixture of 1.1 ml of DMSO and 10 ml of ethanol yields rac.-3-([N-benzyloxycarbonyl-valyl]-amino)-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine; HPLC:tRet(grad20-100/20)=1 4.9; FAB-MS: (M+H)+=494.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. additionethyl acetate is added to the residue
  3. washthe ethyl acetate suspension is washed with 2N HCl solution, sat. NaHCO3 solution and brine
  4. filtrationfinally the insoluble crude product is filtered off
  5. customCrystallization
  6. additionfrom a hot mixture of 1.1 ml of DMSO and 10 ml of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-39901dd3ce8b4193ba5101356d091ad0
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251911B1

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