Water → N-(4-fluorobenzyl)-2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23631Notes

Reaction equation

HRID 23631 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:22])=[C:12]3[S:18][C:17]([CH2:19][OH:20])=[C:16]([CH3:21])[C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[C:25](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[S:18][C:17]([CH2:19][OH:20])=[C:16]([CH3:21])[C:13]=3[N:14]([CH3:25])[CH:15]=2)=[O:9])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178429626HCID 178429626, compound

Product 1

HCID 22574394N-(4-fluorobenzyl)-2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of 3.34 g (9.64 mmol) N-(4-fluorobenzyl)-7-hydroxy-2-(hydroxymethyl)-3-methylthieno[3,2-b]pyridine-6-carboxamide and 1.99 g (14.4 mmol) potassium carbonate in 50 mL anhydrous DMF, was added 0.89 mL (14.3 mmol) iodomethane. The mixture was stirred at room temperature. After 40 minutes the slurry became homogeneous and then cloudy. After another 15 minutes the mixture became a thick slurry that stopped stirring. An additional 30 mL of anhydrous DMF was added and the thick slurry was stirred at room temperature over night. Then, 150 mL of water was added to the slurry and the solids were collected by vacuum filtration and dried in a vacuum oven at 60° C. to provide 3.30 g of title compound as a tan solid.

Workup

  1. waitAfter another 15 minutes the mixture became
  2. stirringa thick slurry that stopped stirring
  3. stirringthe thick slurry was stirred at room temperature over night
  4. filtrationthe solids were collected by vacuum filtration
  5. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-8224447880024544928a451ebc417f23
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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