Cyanogen Bromide → 3-(2-amino-6-phenoxy-4H-quinazolin-3-yl)-N-cyclohexyl-N-methyl-propionamide

HRID 1968776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968776
[NH2:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][C:3]=1[CH2:4][NH:5][CH2:6][CH2:7][C:8]([N:10]([CH3:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].[N:29]#[C:30]Br>C(O)C>[NH2:29][C:30]1[N:5]([CH2:6][CH2:7][C:8]([N:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH3:17])=[O:9])[CH2:4][C:3]2[C:2](=[CH:21][CH:20]=[C:19]([O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:18]=2)[N:1]=1

Komponenten

4

Edukt 2

HCID 10476Cyanogen BromideHCID 586251533-(2-Amino-5-phenoxy-benzylamino)-N-methyl-N-phenyl-propionamide

Produkt 1

HCID 586251423-(2-amino-6-phenoxy-4H-quinazolin-3-yl)-N-cyclohexyl-N-methyl-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-(2-amino-5-phenoxy-benzylamino)-N-methyl-N-phenyl-propionamide (diamine) (1.4 g, 0.0037 mol) and cyanogen bromide (0.58 g, 0.0055 mol) in 70 mL of ethanol was refluxed for 3 h. The solvent was evaporated to yield a residue, which was crystallized from EtOAc (100 mL). The resulting precipitate was dissolved in ethanol and stirred for 3 h. The resulting precipitate was collected by filtration, washed with ethanol, and dried to yield the title product, pure 3-(2-amino-6-phenoxy-4H-quinazolin-3-yl)-N-cyclohexyl-N-methyl-propionamide.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customto yield a residue, which
  3. customwas crystallized from EtOAc (100 mL)
  4. dissolutionThe resulting precipitate was dissolved in ethanol
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with ethanol
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e149b86cc8ac47409f1351c2963b1410
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426429B2

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