Acetyl chloride → n-[4-(4-Aminothieno[3,2-c]pyridin-3-yl)phenyl]acetamide

HRID 1270846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270846
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13]([NH2:17])=[N:14][CH:15]=[CH:16][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.CN1CC[O:22][CH2:21][CH2:20]1.C(Cl)(=O)C>C1COCC1>[NH2:17][C:13]1[C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:21](=[O:22])[CH3:20])=[CH:7][CH:6]=3)=[CH:9][S:10][C:11]=2[CH:16]=[CH:15][N:14]=1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 79724-MethylmorpholineHCID 184507533-(4-Aminophenyl)thieno(3,2-c)pyridin-4-amine

Produkt 1

HCID 18451353n-[4-(4-Aminothieno[3,2-c]pyridin-3-yl)phenyl]acetamideAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A −30° C. solution of Example 17A (0.1 g, 0.41 mmol) and N-methylmorpholine (0.03 mL, 0.41 mmol) in THF (5 mL) was treated dropwise with acetyl chloride (0.03 mL, 0.41 mmol), stirred for 1 hour, warmed to 0° C. over 1 hour, quenched with water, and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 111 mg of the desired product. Rf=0.24 (5% methanol/dichloromethane).

Aufarbeitung

  1. customquenched with water
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5ead2123f8ff4de1af5ca3c31ea6d2a8
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202363B2

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