Ammonia → 3-Anilino-7-(1h-indol-5-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

HRID 2358860

Reaktionsgleichung

Reaktionsgleichung von HRID 2358860
[NH:1]([C:8]1[C:16]2[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][CH:22]=[CH:21]4)[C:11]=2[S:10][C:9]=1[C:27]([O:29]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:32]>C(OC(O)C)C>[NH:1]([C:8]1[C:16]2[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[NH:23][CH:22]=[CH:21]4)[C:11]=2[S:10][C:9]=1[C:27]([NH2:32])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 68457359Ethyl 3-anilino-7-(1h-indol-5-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate

Produkt 1

HCID 684569933-Anilino-7-(1h-indol-5-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 101298981-EthoxyethanolLösungsmittel

Versuchsvorschrift

A mixture of Example 37 (200 mg) and liquid ammonia (5 mL) in ethoxyethanol (10 mL) was heated in a sealed vessel at 80° C. at 400 p.s.i. for 48 h. The solvent was removed in vacuo and purification by column chromatography (silica, 10% to 40% EtOAc in DCM) gave the title compound (42 mg). δH (CDCl3) 9.00 (1H, br s), 8.65 (1H, br s), 7.57 (1H, s), 7.37 (1H, d, J 8.5 Hz), 7.30-7.24 (2H, m), 7.20-7.18 (2H, m), 7.16 (1H, d, J 9.7 Hz), 7.18-6.98 (3H, m), 6.52 (1H, br s), 6.33 (1H, d, J 9.7 Hz), 5.20 (2H, br s). LCMS (ES+) RT 3.77 minutes, 430 (M+H)+. LCMS (ES+) RT 2.93 minutes, 401 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed in vacuo and purification by column chromatography (silica, 10% to 40% EtOAc in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-01cfcae5f1924e2da114e69d0b66c40c
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07763729B2

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