Water → 2-Acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methylpyridin-4-yl)amide

HRID 564735Notes

Reaction equation

HRID 564735 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[C:12]2[CH:21]=[C:20]([C:22](OC)([O:24]C)[CH3:23])[O:19][C:13]=2[C:14]([O:17][CH3:18])=[N:15][CH:16]=1)=[O:10].FC(F)(F)C(O)=O.O>C(Cl)(Cl)Cl.ClCCl>[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[C:12]2[CH:21]=[C:20]([C:22](=[O:24])[CH3:23])[O:19][C:13]=2[C:14]([O:17][CH3:18])=[N:15][CH:16]=1)=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 700816022-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methylpyridin-4-yl)amide

Product 1

HCID 867561882-Acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methylpyridin-4-yl)amideYield 83.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (3-methylpyridin-4-yl)amide (0.15 g), trifluoroacetic acid (0.23 ml) and water (0.50 ml) were stirred at 50° C. in chloroform (20 ml) for 4 h. The mixture was cooled and diluted with dichloromethane (30 ml), washed with saturated sodium bicarbonate solution (30 ml) then water (30 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo to give the title compound (0.11 g) as a cream solid.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with saturated sodium bicarbonate solution (30 ml)
  3. dry with materialwater (30 ml), dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0b1df72aa6ac4ecca8134a7d8c70ac35
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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