Trifluoroacetic acid → 6-acetyl-4-(2-chlorophenyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

HRID 489456Notes

Reaction equation

HRID 489456 reaction equation
COC(OC)(C)C(OC)=O.ClC1C=CC=CC=1C=O.NC1C=CNN=1.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH:33]1[C:38]([C:39]#[N:40])=[C:37]([C:41]([O:45][CH3:46])([O:43][CH3:44])[CH3:42])[NH:36][C:35]2=[N:47][NH:48][CH:49]=[C:34]12.FC(F)(F)C(O)=O>ClCCl>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH:33]1[C:38]([C:39]#[N:40])=[C:37]([C:41]([O:45][CH3:46])([O:43][CH3:44])[CH3:42])[NH:36][C:35]2=[N:47][NH:48][CH:49]=[C:34]12.[C:41]([C:37]1[NH:36][C:35]2=[N:47][NH:48][CH:49]=[C:34]2[CH:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[Cl:26])[C:38]=1[C:39]#[N:40])(=[O:43])[CH3:42]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 69962-ChlorobenzaldehydeHCID 82339Methyl 2,2-dimethoxypropionateHCID 178418806HCID 178418806, compoundHCID 1784962034-(2-chlorophenyl)-6-(1,1-dimethoxyethyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

Product 2

HCID 1784669336-acetyl-4-(2-chlorophenyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrileYield 85.4%HCID 1784962034-(2-chlorophenyl)-6-(1,1-dimethoxyethyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-Chlorophenyl)-5-cyano-4,7-dihydro-6-(1,1-dimethoxyethyl)-2H-pyrazolo[3,4-b]pyridine was prepared from methyl 2,2-dimethoxypropionate, 2-chlorobenzaldehyde and 3-aminopyrazole in the same manner as in Example 1001. To a solution of 4-(2-chlorophenyl)-5-cyano-4,7-dihydro-6-(1,1-dimethoxyethyl)-2H-pyrazolo[3,4-b]pyridine (1.0 g) in dichloromethane (10 mL) was added a trifluoroacetic acid (10 mL) under ice-cooling and the mixture was stirred under ice-cooling for 1 hour. The solvent was evaporated and the obtained residue was crystallized from ethyl acetate to give the title compound (370 mg) as white crystals.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. customThe solvent was evaporated
  4. customthe obtained residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-dab1f6acc3a94d9a84440008e651fd88
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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