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

HRID 2390619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2390619
[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-ddb5987633a148769b0af9a6fed78df7
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273736B2

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