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Sodium borohydride → 3-[2-Amino-6-(hydroxy-phenyl-methyl)-4H-quinazolin-3-yl]-N-cyclohexyl-N-methyl-propionamide

HRID 1968822
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1968822
[NH2:1][C:2]1[N:11]([CH2:12][CH2:13][C:14]([N:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:8]=2)[N:3]=1.[BH4-].[Na+]>CO.C1COCC1>[NH2:1][C:2]1[N:11]([CH2:12][CH2:13][C:14]([N:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:24]([OH:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:8]=2)[N:3]=1
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Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 167412383-(2-Amino-6-benzoylquinazolin-3(4H)-YL)-N-cyclohexyl-N-methylpropanamide

Produkt 1

HCID 586251343-[2-Amino-6-(hydroxy-phenyl-methyl)-4H-quinazolin-3-yl]-N-cyclohexyl-N-methyl-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A mixture of 3-(2-amino-6-benzoyl-4H-quinazolin-3-yl)-N-cyclohexyl-N-methyl-propionamide (0.0056 mol) in methanol (60 mL) and THF (30 mL) was stirred at room temperature. Then, NaBH4 (0.0056 mol) was added and the reaction mixture was stirred for 30 min at room temperature. The solvent was evaporated, and the residue was stirred in H2O and then extracted with CH2Cl2. The organic layer was separated and dried, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: 94:6 CH2Cl2:(CH3OH:NH3)). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 30 min at room temperature
  2. customThe solvent was evaporated
  3. stirringthe residue was stirred in H2O
  4. extractionextracted with CH2Cl2
  5. customThe organic layer was separated
  6. customdried
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: 94:6 CH2Cl2:(CH3OH:NH3))
  9. customThe purest product fractions were collected
  10. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f10a870669544579bd9a421c62e14cd4
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08426429B2

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