Trifluoroacetic acid → 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine

HRID 916215

Reaction equation

HRID 916215 reaction equation
C(OC(=O)[NH:7][C:8]1[N:9]([CH3:26])[N:10]=[C:11]2[C:16]=1[CH2:15][CH2:14][CH2:13][N:12]2[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[Cl:25])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:25][C:18]1[CH:19]=[C:20]([CH3:24])[CH:21]=[C:22]([CH3:23])[C:17]=1[N:12]1[CH2:13][CH2:14][CH2:15][C:16]2=[C:8]([NH2:7])[N:9]([CH3:26])[N:10]=[C:11]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23527225[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]carbamic acid tert-butyl ester

Product 1

HCID 221362787-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 287 mg of [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]carbamic acid tert-butyl ester (Example 8c) in 9 mL of dichloromethane, was added 3 mL of trifluoroacetic acid. After 15 min, the cooling bath was removed and the reaction mixture was allowed to stir and warm to room temperature during 3 h. The reaction mixture was then diluted with dichloromethane and washed with dilute aqueous sodium hydroxide. The aqueous phase was washed with additional dichloromethane, after which the combined organics were dried with magnesium sulfate and concentrated. The residue was chromatographed on silica gel eluting with a methanol/dichloromethane gradient to provide 182 mg of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine, mp 234-236° C.

Workup

  1. customthe cooling bath was removed
  2. additionThe reaction mixture was then diluted with dichloromethane
  3. washwashed with dilute aqueous sodium hydroxide
  4. washThe aqueous phase was washed with additional dichloromethane
  5. dry with materialafter which the combined organics were dried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with a methanol/dichloromethane gradient

Sources & evidence

ORD record
ord-3cbaaaa7e1f54954a9d679f76908f440
Source dataset
uspto-grants-2007_09
Patent number
US07268146B2

Linked notes

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