Potassium Carbonate → N-(4-Chlorobenzyl)-2-(hydroxymethyl)-7-(2-methoxyethyl)-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamide

HRID 2307297Notes

Reaction equation

HRID 2307297 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][O:10][CH3:11].[Cl:12][C:13]1[CH:34]=[CH:33][C:16]([CH2:17][NH:18][C:19]([C:21]2[C:22]([OH:32])=[C:23]3[CH:29]=[C:28]([CH2:30][OH:31])[S:27][C:24]3=[N:25][CH:26]=2)=[O:20])=[CH:15][CH:14]=1>CN(C=O)C.O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][NH:18][C:19]([C:21]2[C:22](=[O:32])[C:23]3[CH:29]=[C:28]([CH2:30][OH:31])[S:27][C:24]=3[N:25]([CH2:8][CH2:9][O:10][CH3:11])[CH:26]=2)=[O:20])=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178522940HCID 178522940, compound

Product 1

HCID 22605694N-(4-Chlorobenzyl)-2-(hydroxymethyl)-7-(2-methoxyethyl)-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (5.0 g) and bromoethylmethyl ether (5.0 g) are added to a solution of N-(4-chlorobenzyl)-4-hydroxy-2-(hydroxymethyl)thieno[2,3-b]pyridine-5-carboxamide (11.4 g, prepared as described in U.S. Pat. No. 6,239,142) in anhydrous DMF (350 mL). The reaction mixture is stirred at room temperature for 18 b. The mixture is diluted with water (600 mL) and filtered. The resulting white powder is dried in a vacuum oven to afford 8.44 g of the title compound as a white solid. Physical characteristics. M.p. 193° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.58, 8.65, 7.37, 7.29, 5.82, 4.70, 4.54, 4.47, 3.76, 3.24. HRMS (FAB) m/z 407.0836 (M+H)+. Anal. Found: C, 55.81; H, 4.71; N, 6.90; Cl, 8.58, S, 7.81.

Workup

  1. customprepared
  2. filtrationfiltered
  3. customThe resulting white powder is dried in a vacuum oven

Sources & evidence

ORD record
ord-f1bb8e5adc354093b2e7b43054b36bad
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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