Hydrochloric Acid → N-(8-Amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-2,2,2-trifluoroacetamide

HRID 355980Notes

Reaction equation

HRID 355980 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([NH2:14])[CH:6]=[C:7]([F:13])[C:8]=2[CH3:12])[C:3]1=[O:15].C(O)C.C([O:21][C:22](=O)[C:23]([F:26])([F:25])[F:24])C.Cl>C(N(CC)CC)C.C1COCC1>[NH2:14][C:5]1[CH:6]=[C:7]([F:13])[C:8]([CH3:12])=[C:9]2[C:4]=1[C:3](=[O:15])[CH:2]([NH:1][C:22](=[O:21])[C:23]([F:26])([F:25])[F:24])[CH2:11][CH2:10]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 9794Ethyl trifluoroacetateHCID 22449502HCID 22449502, compound

Product 1

HCID 22449445N-(8-Amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

The compound obtained in (8) above (1.66 gm) was dissolved into a mixed solvent of 70 ml of ethanol and 10 ml of THF. To the solution were added 2 ml of triethylamine and 1.5 ml of ethyltrifluoroacetate, followed by stirring for 20 hours at 20° C. The reaction product was added to dilute aqueous solution of hydrochloric acid and extracted with chloroform. The extract was washed with water, saturated sodium bicarbonate and saturated brine in this order, and dried over anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was subjected to silica gel column chromatography using chloroform as an eluant to obtain fractions containing the target compound. The fractions were concentrated to obtain 1.79 gm of the title compound.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water, saturated sodium bicarbonate and saturated brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal of the solvent
  5. customby evaporation
  6. customto obtain fractions
  7. additioncontaining the target compound
  8. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-a3be8434b4f84c76907dbada209cd206
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

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