Trifluoroacetic acid → HCID 22293620, compound

HRID 967368Notes

Reaction equation

HRID 967368 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[NH:14][N:15]=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25]>C(Cl)Cl>[F:27][C:26]([F:29])([F:28])[C:24]([O-:30])=[O:25].[Br:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]2[C:10]3[CH2:9][NH:8][CH2:13][CH2:12][C:11]=3[NH2+:14][N:15]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69156804HCID 69156804, compound

Product 1

HCID 22293620HCID 22293620, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 10.0 g (26.4 mmol) of the 3-(4-bromo-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester in CH2Cl2 (26.0 mL) was added 26.0 mL of TFA. The resulting mixture was allowed to stir overnight. The solvent was removed under reduced pressure and the solid was dried in vacuo. The dried solid was suspended in Et2O and stirred vigorously for 2 h and then filtered and dried in vacuo to give 10.1 g of a white solid, which was used without further purification. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.05. MS (electrospray): m/z calculated for C12H12BrN3 [M++H] 278.02, observed 278.0.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe solid was dried in vacuo
  3. stirringstirred vigorously for 2 h
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-1cc6c69c86e34b1c9de47d2f04a29940
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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