Ammonia → 3-Anilino-4-methyl-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

HRID 2358863

Reaktionsgleichung

Reaktionsgleichung von HRID 2358863
[NH:1]([C:8]1[C:16]2[C:15]([CH3:17])=[CH:14][C:13](=[O:18])[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[S:10]C=1C(OCC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:33]([OH:35])[CH3:34])C.[NH3:36]>>[NH:1]([C:8]1[C:16]2[C:15]([CH3:17])=[CH:14][C:13](=[O:18])[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[S:10][C:34]=1[C:33]([NH2:36])=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 222AmmoniaHCID 101298981-EthoxyethanolHCID 68457883Ethyl 3-anilino-4-methyl-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate

Produkt 1

HCID 684552193-Anilino-4-methyl-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamideAusbeute 66 %

Versuchsvorschrift

A mixture of Example 97 (150 mg, 0.37 mmol), ethoxyethanol and liquid ammonia was heated in a sealed vessel at 80° C. at 400 psi for 16 h. The mixture was concentrated in vacuo and the solid recrystallised from MeOH to give the title compound as a yellow solid (92 mg, 66%). δH (DMSO-d6) 8.05 (1H, s), 7.68-7.59 (3H, m), 7.53-7.51 (2H, m), 7.5 (1H, br), 7.24-7.20 (2H, m), 6.80 (1H, t, J 7.3 Hz), 6.64 (2H, d, J 7.7 Hz), 6.29 (1H, s), 2.22 (3H, s). LCMS (ES+) RT 3.074 minutes, 375.9 (M+H)+

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe solid recrystallised from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-292b757483e14a25932c31ec1bd8c56f
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07763729B2

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