Trifluoroacetic acid → HCID 22248602, compound

HRID 890122Notes

Reaction equation

HRID 890122 reaction equation
C([O:5][C:6]1[C:7]([CH:12](F)[N:13]2[CH2:18][CH2:17][CH:16]([C:19](=[O:28])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[CH2:15][CH2:14]2)=[N:8][CH:9]=[CH:10][N:11]=1)(C)(C)C.[F:30]C(F)(F)C(O)=O>>[F:30][C:10]1[NH:11][C:6](=[O:5])[C:7]([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([C:19](=[O:28])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[CH2:15][CH2:14]2)=[N:8][CH:9]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22248069HCID 22248069, compound

Product 1

HCID 22248602HCID 22248602, compoundYield 93%

Procedure

After dissolving 122 mg of 1-[1-(3-tert-butoxy-fluoro-2-pyrazinylmethyl)piperidin-4-yl]-2-(2-fluorophenyl)ethanone in 3 ml of trifluoroacetic acid, the mixture was stirred for 1.5 hours at room temperature. The reaction solution was cooled on ice, the pH was adjusted to 7 with a 5% sodium hydroxide solution, and extraction was performed with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Diethyl ether was added to the residue and the mixture was filtered to obtain the title compound (97 mg, 93% yield).

Workup

  1. temperatureThe reaction solution was cooled on ice
  2. extractionthe pH was adjusted to 7 with a 5% sodium hydroxide solution, and extraction
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionDiethyl ether was added to the residue
  6. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-567271fea0b74b8ba946ab013457c39f
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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