Pyridine → HCID 4709, Verbindung

HRID 1617278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617278
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:29])[CH2:27][CH3:28]>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:26](=[O:29])[CH2:27][CH3:28])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Produkt 1

HCID 4709HCID 4709, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

N4-(3-bromophenyl)quinazoline-4,6-diamine (100 mg, 0.32 mmol), pyridine (0.3 mL), and DMAP (20 mg) were dissolved in 10 mL of anhydrous THF. The solution was cooled to 5° C. Propionyl chloride (33 mg, 0.35 mmol) was added to the reaction flask dropwise. Ice bath removed was removed, and the reaction mixture was stirred at room temperature and filtered. The filtrate was dried in vacuo to give a yellow solid. The yellow solid was dissolved in ethyl acetate, washed once with saturated Na2CO3, then with 10% acetic acid, and then with brine. The organic phase was dried, filtered, and stripped of solvent in vacuo to give a crude product which was purified by TLC to give the title compound as a whitish product.

Aufarbeitung

  1. customIce bath removed
  2. customwas removed
  3. filtrationfiltered
  4. customThe filtrate was dried in vacuo
  5. customto give a yellow solid
  6. washwashed once with saturated Na2CO3
  7. customThe organic phase was dried
  8. filtrationfiltered
  9. customto give a crude product which
  10. customwas purified by TLC

Quellen und Nachweise

ORD-Eintrag
ord-b81dd0dd7fce4a62abd7031f36a2f462
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765946B2

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