Trifluoroacetic acid → HCID 117988120, compound

HRID 2206249Notes

Reaction equation

HRID 2206249 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([O:18][CH3:19])[C:12]=2[C:11]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)=[N:10]1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([O:18][CH3:19])[C:12]=2[C:11]([C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)=[CH:24][CH:25]=2)=[N:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117987612HCID 117987612, compound

Product 1

HCID 117988120HCID 117988120, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)phenyl)piperazine-1-carboxylate (920 mg) in dichloromethane (10 mL) was added trifluoroacetic acid (4 mL) under ice-cooling, and the mixture was stirred at room temperature for 5 hr, and concentrated under reduced pressure. The residue was diluted with dichloromethane, and the mixture was adjusted to pH=9 with saturated aqueous sodium carbonate solution, and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (744 mg).

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-622a921038e7428babe14f29043d56b8
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

Loading…