Hydrochloric Acid → 3-Chloro-N-{2-methyl-3-[3-(methyloxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-4-yl}benzenesulfonamide

HRID 573690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573690
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([O:18]C)[N:15]=[C:14]3[S:20][C:21]([CH3:31])=[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:13]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)=[C:21]([CH3:31])[S:20][C:14]=3[NH:15][C:16](=[O:18])[CH:17]=2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 683237633-Chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

Produkt 1

HCID 683238243-Chloro-N-{2-methyl-3-[3-(methyloxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-4-yl}benzenesulfonamideAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Alternatively, a solution of 3-chloro-N-{2-methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide (Example 115) (710 mg, 1.495 mmol) in 37% HCl (8 mL, 97 mmol) was heated to 100° C. under nitrogen atmosphere overnight. The reaction mixture was cooled to RT, diluted with DCM (ca. 50 mL) and washed with water (ca. 50 mL×2). The combined aqueous layer was re-extracted with DCM (ca. 25 mL) and the combined organic layers passed through phase separator and the solvent concentrated in vacuo. The residue was further triturated with DCM, to afford the title compound (407 mg).

Aufarbeitung

  1. washwashed with water (ca. 50 mL×2)
  2. extractionThe combined aqueous layer was re-extracted with DCM (ca. 25 mL)
  3. concentrationthe solvent concentrated in vacuo
  4. customThe residue was further triturated with DCM

Quellen und Nachweise

ORD-Eintrag
ord-d8673b562dac4012a33348128e2f778a
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029545B2

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