Triethylamine → HCID 10832923, Verbindung

HRID 394748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394748
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.CCN(CC)CC.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29]>CN(C1C=CN=CC=1)C.O>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:8]2[C:9]3[CH:10]=[N:11][C:2]([NH:1][C:27](=[O:30])[CH:28]=[CH2:29])=[CH:3][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 3820597-Amino-4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidine

Produkt 1

HCID 10832923HCID 10832923, VerbindungAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a stirred solution of 7-amino-4-[(3- bromophenyl)amino]pyrido[4,3-d]pyrimidine (J Med Chem, 1995;38:3780) (140 mg, 0.46 mmol), DMAP (14 mg) and Et3N (excess, 2.0 mL) at 0° C. under N2 was added acryloyl chloride (4.8 mol eq., 182 μL) dropwise over 4 hours. The reaction was then stirred at 20° C. diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure before being chromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (5:45:50), to give N-[4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidin-7-yl]-acrylamide (12 mg, 7%) as a cream powder, mp (CH2Cl2/hexane) 215-220° C. (dec).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custombefore being chromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (5:45:50)

Quellen und Nachweise

ORD-Eintrag
ord-539664977271424a9f4c39a705bb7db6
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602863B1

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