Potassium Carbonate → HCID 178457659, compound

HRID 2075509Notes

Reaction equation

HRID 2075509 reaction equation
Cl.[NH2:2][OH:3].[C:4]([C:6]([NH:9][C:10]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:22][CH2:23][C:24]1[CH:25]=[N:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=1)=[O:11])([CH3:8])[CH3:7])#[N:5].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[OH:3][NH:2][C:4]([C:6]([NH:9][C:10]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:22][CH2:23][C:24]1[CH:25]=[N:26][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:28][CH:29]=1)=[O:11])([CH3:8])[CH3:7])=[NH:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 66701115HCID 66701115, compound

Product 1

HCID 178457659HCID 178457659, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.16 g hydroxylamine hydrochloride was added to a room temperature solution of 0.28 g 1-(6-trifluoromethyl-pyridin-3-yl-methoxy)-naphthalene-2-carboxylic acid (cyano-dimethyl-methyl)-amide and 0.50 g potassium carbonate in 5 ml 95% ethanol, and the resulting mixture was heated at reflux for 24 h. The reaction mixture was cooled to room temperature, diluted with 100 ml ethyl acetate, and was washed twice with 100 ml sat. sodium hydrogen carbonate solution and 100 ml brine. The combined organic layers were dried over sodium sulphate, and concentrated in vacuo to give an orange oil. Purification of the residue by RP-HPLC afforded 0.031 g of 1-(6-trifluoromethyl-pyridin-3-yl-methoxy)-naphthalene-2-carboxylic acid [1-(N-hydroxycarbamimidoyl)-1-methyl-ethyl]-amide as a colorless foam.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 24 h
  3. washwas washed twice with 100 ml sat. sodium hydrogen carbonate solution and 100 ml brine
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customto give an orange oil
  7. customPurification of the residue by RP-HPLC

Sources & evidence

ORD record
ord-5cdec31eb0534423ab96a08fdf19490c
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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