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Hydrochloric Acid → (4-Benzyloxy-phenyl)-(-6-(3-methylisoxazol-5-yl)-quinazolin-4-yl)-amine hydrochloride

HRID 1936809
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1936809
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[CH:27])[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:28]([CH2:31][CH3:32])([O-])=[O:29].C1(N=C=O)C=CC=CC=1.[ClH:42]>C(N(CC)CC)C.C(OCC)(=O)C.ClCCl>[ClH:42].[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]4[O:29][N:28]=[C:31]([CH3:32])[CH:27]=4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 22609768(4-Benzyloxy-phenyl)(6-ethynylquinazolin-4-yl)-amine

Produkt 1

HCID 22609788(4-Benzyloxy-phenyl)-(-6-(3-methylisoxazol-5-yl)-quinazolin-4-yl)-amine hydrochlorideAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8471TriethylamineKatalysator
HCID 6344DichloromethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A stirred mixture of (4-benzyloxy-phenyl)-(6-ethynylquinazolin-4-yl)-amine (0.20 g, 0.57 mmol), nitroethane (0.20 g, 2.7 mmol), phenylisocyanate (0.15 ml, 0.164 g, 1.38 mmol), and triethylamine (3 drops) in a mixture of ethyl acetate (10 ml) and dichloromethane (5 ml) was heated at reflux for 18 hours. After cooling the mixture was filtered to remove solid, and the concentrated filtrate was purified by silica gel chromatography, eluting with 50% ethyl acetate/i-hexane. After concentration of the appropriate fractions, the material obtained was treated with methanolic HCl, the solvent was removed in vacuo and the residue was triturated with ether to give the title compound as a yellow solid (0.027 g, 0.061 mmol, 11%); δH [2H6]DMSO 12.0 (1H,s), 9.55 (1H,s), 8.91 (1H,s), 8.48 (1H,d), 8.03 (1H,d), 7.68 (2H,d), 7.32-7.55 (5H,m), 7.22 (1H,s), 7.15 (2H,d), 5.18 (2H,s), 2.35 (3H,s); m/z (M+1+) 409.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling the mixture
  4. filtrationwas filtered
  5. customto remove solid
  6. customthe concentrated filtrate was purified by silica gel chromatography
  7. washeluting with 50% ethyl acetate/i-hexane
  8. customAfter concentration of the appropriate fractions, the material obtained
  9. customthe solvent was removed in vacuo
  10. customthe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-9fb7cd1284144383ac253d6301399840
Quelldatensatz
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06391874B1

Notizen zur Reaktion

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