Triethylamine → N-{3-Cyano-4-[(3,4-difluorophenyl)amino]-6-quinolinyl}-2-propenamide

HRID 612091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612091
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32].C(=O)(O)[O-].[Na+]>CN(C=O)C.C1COCC1>[C:12]([C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=1)=[CH:3][C:2]([NH:1][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:11][CH:10]=2)#[N:13]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 224665706-Amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile

Produkt 1

HCID 22466577N-{3-Cyano-4-[(3,4-difluorophenyl)amino]-6-quinolinyl}-2-propenamideAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolved 1.00 g (3.37 mmol) 6-amino-4-[(3,4-difluorophenyl)amino]-3-quinolinecarbonitrile in 2 ml DMF, added 12 ml THF, and chilled to 0° C. under N2. Added 517 μl (3.71 mmol) triethylamine and 310 μl (3.72 mmol) acryloyl chloride. Removed ice bath a 15 minutes. At 3.5 hours stripped solvent and slurried residue with dilute sodium bicarbonate. Collected solids, washed with water, and air dried. Boiled in ethyl acetate, collected solids and dried in vacuo, giving 332 mg of yellow solid: mass spectrum (electrospray m/e): M+H=351.1.

Aufarbeitung

  1. customa 15 minutes
  2. customCollected solids
  3. washwashed with water, and air
  4. customdried
  5. customcollected solids
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3d4e6c9d625a473dac46cead941dea58
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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