Reaction equation
[OH:1][CH2:2][C:3]1[S:11][C:10]2[C:9](=[O:12])[C:8]([C:13]([O:15]CC)=O)=[CH:7][N:6]([CH3:18])[C:5]=2[C:4]=1[CH3:19].[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.C[O-].[Na+]>CO>[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:26][C:13]([C:8]2[C:9](=[O:12])[C:10]3[S:11][C:3]([CH2:2][OH:1])=[C:4]([CH3:19])[C:5]=3[N:6]([CH3:18])[CH:7]=2)=[O:15])=[CH:23][CH:22]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of ethyl 2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (627 mg, 2.23 mmol), 4-chlorobenzylamine (2.0 mL, 16.4 mmol), 0.5 M sodium methoxide in methanol (25 mL, 8.92 mmol) and methanol (10 mL) was stirred under nitrogen in a tightly capped 250 mL round bottom flask at 50° C. for 24 hours. The initial solution slowly dropped a thick white precipitate during the reaction. After cooling to room temperature, the mixture was filtered, and the collected solid was washed with methanol and dried in vacuo, leaving a white solid. The crude solid was suspended in boiling methanol (200 mL), cooled to room temperature, and filtered, to give the title compound as a white powder (585 mg).
Workup
- customduring the reaction
- filtrationthe mixture was filtered
- washthe collected solid was washed with methanol
- customdried in vacuo
- customleaving a white solid
- temperaturecooled to room temperature
- filtrationfiltered
Sources & evidence
- ORD record
- ord-9e59478c9ad84d828ec914ab1d191438
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06852731B2
Linked notes
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