Water → N-(4-Chlorobenzyl)-4-ethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 982702Notes

Reaction equation

[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:19])=[C:12]3[S:18][CH:17]=[CH:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:29][CH3:30].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:19])[C:12]3[S:18][CH:17]=[CH:16][C:13]=3[N:14]([CH2:29][CH3:30])[CH:15]=2)=[O:9])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N-(4-chlorobenzyl)-7-hydroxythieno[3,2-b]pyridine-6-carboxamide (Example 1, 885 mg)was dissolved in DMF (20 mL) and to the solution was added potassium carbonate (1.92 g) and iodoethane (1.1 mL). The mixture was heated to 100° C. for 16 h. After cooling to room temperature, the reaction mixture was poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with water (3×25 mL) followed by brine (25 mL), dried (MgSO4), and concentrated. The crude product was purified by column chromatography (EtOAc/heptane, 1/1; CH2Cl2/methanol, 100/1) and the resulting solid was recrystallized from ethanol to afford 590 mg of the title compound as a white solid.

Workup

temperatureAfter cooling to room temperature
extractionextracted with EtOAc (3×100 mL)
washThe combined organic layers were washed with water (3×25 mL)
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude product was purified by column chromatography (EtOAc/heptane, 1/1; CH2Cl2/methanol, 100/1)
customthe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record: ord-2ffb984481b8425faab0d6ab3df25328
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06861438B2

Reaction notes

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