Water → N-(4-Chlorobenzyl)-7-methyl-2-(4-morpholinyl-carbonyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

HRID 1978970Notes

Reaction equation

HRID 1978970 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:27])=[C:12]3[CH:18]=[C:17]([C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:20])[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[C:30](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:27])[C:12]3[CH:18]=[C:17]([C:19]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[O:20])[S:16][C:13]=3[N:14]([CH3:30])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522941HCID 178522941, compound

Product 1

HCID 10095064N-(4-Chlorobenzyl)-7-methyl-2-(4-morpholinyl-carbonyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamideYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-(4-morpholinylcarbonyl)thieno[2,3-b]pyridine-5-carboxamide (0.527 g) from Example No. 47 in DMF (10 mL) is added potassium carbonate (0.337 g) followed by iodomethane (0.11 mL). The reaction mixture is stirred at room temperature for 1 h. The reaction mixture is then poured into water (25 mL). The resulting off-white solid is filtered off and recrystallized from acetonitrile to yield 0.448 g (82%) of the title compound as a white solid.

Workup

  1. filtrationThe resulting off-white solid is filtered off
  2. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-f0f40e4c0c584b08bb77fe7a83f269a6
Source dataset
uspto-grants-2001_05
Patent number
US06239142B1

Reaction notes

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