N-Methylaniline → 4-Chloro-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

HRID 497936Notes

Reaction equation

HRID 497936 reaction equation
O[C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]2[N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:12]=[C:13]([CH3:14])[C:3]=12.P(Cl)(Cl)([Cl:23])=O.[CH3:26][NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>O1CCCC1>[Cl:23][C:2]1[C:7]([C:8]([N:27]([CH3:26])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:10])=[CH:6][N:5]=[C:4]2[N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:12]=[C:13]([CH3:14])[C:3]=12

Participants

6

Reactant 4

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178433901HCID 178433901, compound

Product 1

HCID 223202774-Chloro-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamideYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-hydroxy-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (2.0 g, 7.4 mmol) in phosphorous oxychloride (15 mL, 63 mmol) was heated and stirred at 100° C. for 3 hours. After the solution was cooled to room temperature, the solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (50 mL). To the solution, a solution of N-methylaniline (1.0 mL, 9.2 mmol) and triethylamine (5.2 mL, 37 mmol) in tetrahydrofuran (10 mL) was added at 0° C. After the mixture was stirred at room temperature for 1.5 hours, the reaction solvent was evaporated under reduced pressure. Purification of the residue thus obtained by silica gel chromatography (chloroform:methanol=50:1 to 20:1) gave the title compound (2.14 g, 76% yield).

Workup

  1. temperatureAfter the solution was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in tetrahydrofuran (50 mL)
  4. stirringAfter the mixture was stirred at room temperature for 1.5 hours
  5. customthe reaction solvent was evaporated under reduced pressure
  6. customPurification of the residue
  7. customthus obtained by silica gel chromatography (chloroform:methanol=50:1 to 20:1)

Sources & evidence

ORD record
ord-8754d2e208d74794a8391091af0ed37a
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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