p-Toluenesulfonic acid monohydrate → HCID 86630642, compound

HRID 1667967Notes

Reaction equation

HRID 1667967 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:17]=[CH:18][C:19]([CH3:32])=[C:20]([NH:22][C:23]([C:25]5[N:29]([CH3:30])[N:28]=[C:27]([CH3:31])[CH:26]=5)=[O:24])[CH:21]=4)=[N:11][N:10]3[CH:33]=2)=[O:5])[CH2:3][CH2:2]1.O.[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41]([OH:44])(=[O:43])=[O:42])=[CH:37][CH:36]=1>C(O)C>[C:35]1([CH3:45])[CH:36]=[CH:37][C:38]([S:41]([OH:44])(=[O:42])=[O:43])=[CH:39][CH:40]=1.[CH:1]1([C:4]([NH:6][C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:17]=[CH:18][C:19]([CH3:32])=[C:20]([NH:22][C:23]([C:25]5[N:29]([CH3:30])[N:28]=[C:27]([CH3:31])[CH:26]=5)=[O:24])[CH:21]=4)=[N:11][N:10]3[CH:33]=2)=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 24767976Tak-593

Product 1

HCID 86630642HCID 86630642, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide (2.00 g, 4.49 mmol) was added ethanol (80 mL), and the mixture was heated to 70° C. to give a uniform solution. p-Toluenesulfonic acid monohydrate (0.90 g, 4.71 mmol) was added to the mixture, and the mixture was naturally cooled to room temperature. The solvent was evaporated under reduced pressure. To the obtained residue was added hexane/ethanol (3/1, 40 mL), and the mixture was stirred at room temperature for 2 hr. The precipitated crystals were collected by filtration, and washed with hexane/ethanol (3:1). The obtained crystals were dissolved in ethanol (40 mL) by heating and the mixture was naturally cooled to room temperature. The precipitated crystals were collected by filtration and washed with ethanol. The crystals were dried at 70° C. for 3 hr under reduced pressure to give the title compound (2.34 g, 84%) as white crystals.

Workup

  1. customto give a uniform solution
  2. temperaturethe mixture was naturally cooled to room temperature
  3. customThe solvent was evaporated under reduced pressure
  4. additionTo the obtained residue was added hexane/ethanol (3/1, 40 mL)
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with hexane/ethanol (3:1)
  7. dissolutionThe obtained crystals were dissolved in ethanol (40 mL)
  8. temperatureby heating
  9. temperaturethe mixture was naturally cooled to room temperature
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with ethanol
  12. customThe crystals were dried at 70° C. for 3 hr under reduced pressure

Sources & evidence

ORD record
ord-b7db660df92a40efb76d0727b19dcbe1
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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