Pyridine → HCID 21948258, compound

HRID 1593682Notes

Reaction equation

HRID 1593682 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].[NH2:16][C:17]1[C:25]2[C:20](=C[N:22]=[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=3[F:33])[CH:24]=2)[NH:19][N:18]=1.[N:34]1C=CC=CC=1>>[CH2:1]([N:3]([CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH:34][C:20]2[C:25]3[C:17](=[N:16][N:22]=[C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=4[F:33])[CH:24]=3)[NH:18][N:19]=2)=[O:12])=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 3052787Benzoyl chloride, 4-((diethylamino)methyl)-HCID 219482673-amino-5-(2,3-difluorophenyl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 21948258HCID 21948258, compound

Procedure

4-Diethylaminomethylbenzoyl chloride (0.503 g, 2.43 mmol) was added to a solution of 3-amino-5-(2,3-difluorophenyl)-1H-pyrazolo[3,4-c]pyridine (Description 14; 0.200 g, 0.81 mmol) in pyridine (5 mL). The mixture was heated at reflux for 16 hours then the solvent was removed under reduced pressure. The residue was azeotroped, firstly with water and then with ethanol. The resulting solid was dissolved in dimethylformamide and purified initially by preparative HPLC on a C18 column, using a gradient elution with 10-90% v/v of acetonitrile (containing 0.01% trifluoroacetic acid) and water (containing 0.1% trifluoroacetic acid). Subsequent purification by silica gel chromatography using initially 5% v/v methanol in dichloromethane as eluent, followed by 5% v/v 1N methanolic ammonia in dichloromethane as eluent afforded the title compound, a solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was azeotroped, firstly with water
  5. dissolutionThe resulting solid was dissolved in dimethylformamide
  6. custompurified initially by preparative HPLC on a C18 column
  7. washa gradient elution with 10-90% v/v of acetonitrile (containing 0.01% trifluoroacetic acid) and water (containing 0.1% trifluoroacetic acid)
  8. customSubsequent purification by silica gel chromatography

Sources & evidence

ORD record
ord-566f5ffff85f46dd9890bf285855367e
Source dataset
uspto-grants-2007_11
Patent number
US07297792B2

Reaction notes

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