Lithium hydroxide, monohydrate → Ammonium 6-oxo-3-(phenylamino)-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate

HRID 30422

Reaktionsgleichung

O.[OH-].[Li+].[C:4]1([NH:10][C:11]2[C:19]3[CH:18]=[CH:17][C:16](=[O:20])[N:15]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:14]=3[S:13][C:12]=2[C:27]([O:29]CC)=[O:28])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1.O>[O:20]=[C:16]1[N:15]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:14]2[S:13][C:12]([C:27]([O-:29])=[O:28])=[C:11]([NH:10][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:19]=2[CH:18]=[CH:17]1.[NH4+:10]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Lithium hydroxide monohydrate (302 mg, 7.2 mmol) was added to a suspension of the compound of Example 1 (1.49 g, 3.6 mmol) in THF (20 mL) and water (20 mL) and the mixture heated at 60° C. for 18 h. The reaction was cooled to r.t. and bulk of THF removed in vacuo. The remaining concentrate was diluted with saturated ammonium chloride(aq) (50 mL) and the solid precipitate filtered and washed with water (2×20 mL), Et2O (2×20 mL) and dried in vacuo to give the title compound as a white solid in quantitative yield. LCMS (ES+) RT 3.24 minutes, 363 (M+H)+.

Aufarbeitung

temperatureThe reaction was cooled to r.t.
custombulk of THF removed in vacuo
concentrationThe remaining concentrate
additionwas diluted with saturated ammonium chloride(aq) (50 mL)
filtrationthe solid precipitate filtered
washwashed with water (2×20 mL), Et2O (2×20 mL)
customdried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-96c6c57a62254743ad54133be0bc3e7b
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07423047B2

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