Trifluoroacetic acid → HCID 68309869, compound

HRID 2171699Notes

Reaction equation

HRID 2171699 reaction equation
C([O:5][C:6]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][Si](C(C)(C)C)(C)C)[C:19]=3[F:33])[CH2:14][CH2:13]2)[CH:9]=[CH:8][N:7]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:33][C:19]1[C:20]([CH2:24][OH:25])=[CH:21][CH:22]=[CH:23][C:18]=1[N:15]1[CH2:16][CH2:17][N:12]([C:10]2[CH:9]=[CH:8][NH:7][C:6](=[O:5])[CH:11]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86686242HCID 86686242, compound

Product 1

HCID 68309869HCID 68309869, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-tert-Butoxypyridin-4-yl)-4-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]piperazine (3.14 g) was mixed with CH2Cl2 (50 ml), and TFA (5.1 ml) was added thereto, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was mixed with MeOH (2 ml). A 8 M NH3/MeOH solution (10 ml) was added thereto at 0° C., followed by stirring at room temperature for 2 hours. The solid in the reaction mixture was collected by filtration, washed with MeOH, and dried at 50° C. under reduced pressure to obtain 4-{4-[2-fluoro-3-(hydroxymethyl)phenyl]piperazin-1-yl}pyridin-2(1H)-one (1.76 g).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was mixed with MeOH (2 ml)
  4. additionA 8 M NH3/MeOH solution (10 ml) was added
  5. customat 0° C.
  6. stirringby stirring at room temperature for 2 hours
  7. filtrationThe solid in the reaction mixture was collected by filtration
  8. washwashed with MeOH
  9. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-c09a940afa464f5ab5c0e29e7bc1b5ec
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

Loading…