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

HRID 2307293Notes

Reaction equation

HRID 2307293 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH3:9].[Cl:10][C:11]1[CH:32]=[CH:31][C:14]([CH2:15][NH:16][C:17]([C:19]2[C:20]([OH:30])=[C:21]3[CH:27]=[C:26]([CH2:28][OH:29])[S:25][C:22]3=[N:23][CH:24]=2)=[O:18])=[CH:13][CH:12]=1>CN(C=O)C.O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH:16][C:17]([C:19]2[C:20](=[O:30])[C:21]3[CH:27]=[C:26]([CH2:28][OH:29])[S:25][C:22]=3[N:23]([CH2:8][CH3:9])[CH:24]=2)=[O:18])=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178522940HCID 178522940, compound

Product 1

HCID 22605725N-(4-chlorobenzyl)-7-ethyl-2-(hydroxymethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.87 g) and iodoethane (0.5 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 18 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 1.64 g of the title compound as a white solid. Physical characteristics. M.p. 169-172° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.65, 8.74, 7.37, 7.29, 5.81, 4.70, 4.54, 4.32, 1.44. HRMS (FAB) m/z 377.0720 (M+H)+. Anal. Found. C, 56.87; H, 4.77; N, 7.38; Cl, 9.35; S, 8.44.

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-7793c369f8b94e9d9d2db824bc0f186b
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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