Acetic Acid → HCID 89586116, compound

HRID 1747836Notes

Reaction equation

HRID 1747836 reaction equation
[CH3:1][C:2]([NH:13][C:14]([C:16]1[C:21](=[O:22])[C:20]([O:23][CH3:24])=[CH:19][N:18]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[N:17]=1)=O)([CH3:12])[C:3](=[O:11])[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([O-])(=O)C.[Na+].C(O)(=O)C>O>[CH3:1][C:2]1([CH3:12])[C:3](=[O:11])[N:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:14]([C:16]2[C:21](=[O:22])[C:20]([O:23][CH3:24])=[CH:19][N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)[N:17]=2)=[N:13]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 89586428HCID 89586428, compound

Product 1

HCID 89586116HCID 89586116, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-[1,1-dimethyl-2-oxo-2-(phenylamino)ethyl]-5-methoxy-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide (142 mg), sodium acetate (74 mg) and acetic acid (1 mL) was irradiated with microwave at 120° C. for 2 hr. After cooling to room temperature, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (37 mg).

Workup

  1. customwas irradiated with microwave at 120° C. for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-8182dbdb7a534840b767b29ae7374e9f
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

Loading…