HCID 22248182, compound → HCID 22248602, compound

HRID 914917Notes

Reaction equation

HRID 914917 reaction equation
C([O:5][C:6]1[C:7]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20](=[O:29])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[CH2:16][CH2:15]2)=[N:8][CH:9]=[C:10]([F:12])[N:11]=1)(C)(C)C>FC(F)(F)C(O)=O>[F:12][C:10]1[NH:11][C:6](=[O:5])[C:7]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20](=[O:29])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[CH2:16][CH2:15]2)=[N:8][CH:9]=1

Participants

3

Reactant 1

HCID 22248182HCID 22248182, compound

Product 1

HCID 22248602HCID 22248602, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

After dissolving 122 mg of 1-[1-(3-tert-butoxy-5-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-c9b4426b217b40f482e4e31fc23c6c38
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

Loading…