2,4,6-Trimethylbenzoyl chloride → HCID 21948251, compound

HRID 2214746Notes

Reaction equation

HRID 2214746 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4](Cl)=[O:5].[F:13][C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[C:21]1[CH:22]=[C:23]2[C:29]([NH2:30])=[N:28][NH:27][C:24]2=[N:25][N:26]=1>N1C=CC=CC=1>[F:13][C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[C:21]1[CH:22]=[C:23]2[C:29]([NH:30][C:4](=[O:5])[C:3]3[C:2]([CH3:1])=[CH:10][C:9]([CH3:11])=[CH:8][C:7]=3[CH3:12])=[N:28][NH:27][C:24]2=[N:25][N:26]=1

Participants

4

Reactant 2

HCID 970382,4,6-Trimethylbenzoyl chlorideHCID 73855606HCID 73855606, compound

Product 1

HCID 21948251HCID 21948251, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,4,6-Trimethylbenzoyl chloride (0.594 g, 3.24 mmol) was added to a solution of 5-(2,3-Difluorophenyl)-1H-pyrazolo[3,4-c]pyridazin-3-ylamine (Description 14; 0.400 g, 1.62 mmol) in pyridine (2 mL). The solution was heated at reflux for 72 hours, and the solvent then evaporated in vacuo. Piperidine (50 mL) was added and the solution stirred at room temperature for 16 hours. The mixture was evaporated and the residue azeotroped with ethanol. The crude product was purified firstly by chromatography on silica gel using a gradient elution with 5–20% v/v methanol in dichloromethane, and subsequently by further chromatography on silica gel using diethyl ether as eluent to afford the title compound, a solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 72 hours
  3. customthe solvent then evaporated in vacuo
  4. additionPiperidine (50 mL) was added
  5. customThe mixture was evaporated
  6. customthe residue azeotroped with ethanol
  7. customThe crude product was purified firstly by chromatography on silica gel using
  8. washa gradient elution with 5–20% v/v methanol in dichloromethane

Sources & evidence

ORD record
ord-4c6b4843cff54263a6a177baf29c3032
Source dataset
uspto-grants-2006_09
Patent number
US07109199B2

Reaction notes

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