Potassium Carbonate → N-(4-chlorobenzyl)-7-propyl-2-(hydroxymethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

HRID 2307294Notes

Reaction equation

HRID 2307294 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH3:10].[Cl:11][C:12]1[CH:33]=[CH:32][C:15]([CH2:16][NH:17][C:18]([C:20]2[C:21]([OH:31])=[C:22]3[CH:28]=[C:27]([CH2:29][OH:30])[S:26][C:23]3=[N:24][CH:25]=2)=[O:19])=[CH:14][CH:13]=1>CN(C=O)C.O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][NH:17][C:18]([C:20]2[C:21](=[O:31])[C:22]3[CH:28]=[C:27]([CH2:29][OH:30])[S:26][C:23]=3[N:24]([CH2:8][CH2:9][CH3:10])[CH:25]=2)=[O:19])=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178522940HCID 178522940, compound

Product 1

HCID 22605728N-(4-chlorobenzyl)-7-propyl-2-(hydroxymethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.91 g) and 1-iodopropane (0.64 mL) are added to a solution of N-(4-chlorobenzyl)-4-hydroxy-2-(hydroxymethyl)thieno[2,3-b]pyridine-5-carboxamide (2.0 g, prepared as described in U.S. Pat. No. 6,239,142) in anhydrous DMF (60 mL). The reaction mixture is stirred at room temperature for 4 h. The mixture is diluted with water (150 mL) and filtered. The resulting white powder is washed with water (15 mL) followed by diethyl ether (15 mL) and dried in a vacuum oven to afford 1.73 g of the title compound as a white solid Physical characteristics. Mp 174-175° C. 1H NMR (300 MHz, DMSO-d6) δ 10.62, 8.72, 7.38, 7.29, 5.80, 4.69, 4.55, 4.27, 1.87, 0.89; Anal. Found: C, 58.20; H, 4.96; N. 7.13; Cl, 8.98; S, 8.16.

Workup

  1. customprepared
  2. filtrationfiltered
  3. washThe resulting white powder is washed with water (15 mL)
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-39afb4584710432a8940cfc325c4ad3c
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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