Methanesulfonic Acid → N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide methanesulfonate

HRID 2391283

反応式

HRID 2391283 の反応式
[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]([F: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.[CH3:34][S:35]([OH:38])(=[O:37])=[O:36]>C(O)C>[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].[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]([F: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

参加物

4

反応物 2

HCID 6395Methanesulfonic AcidHCID 24767979N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

生成物 1

HCID 86630647N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide methanesulfonate収率 26.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide (1.00 g, 2.23 mmol) in ethanol (50 ml) was stirred at 70° C. for 20 min. Methanesulfonic acid (0.17 mL, 2.33 mmol) was added to the mixture, and the mixture was further stirred for 10 min. The mixture was naturally cooled to room temperature, and 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 precipitate was collected by filtration, and washed with hexane/ethanol (3:1). The obtained precipitate was dissolved in ethanol (40 mL) by heating, and the mixture was naturally cooled to room temperature. The precipitated crystals were collected by filtration, ethyl acetate (20 mL) was added to the mixture, and the mixture was stirred at 80° C. by heating. After cooling the mixture to room temperature, the precipitate was collected by filtration, washed with ethyl acetate and dried under reduced pressure at 100° C. for 3 hr to give the title compound (0.32 g, 26%) as white crystals.

後処理

  1. customthe solvent was evaporated under reduced pressure
  2. additionTo the obtained residue was added hexane/ethanol (3:1, 40 mL)
  3. stirringthe mixture was stirred at room temperature for 2 hr
  4. filtrationThe precipitated precipitate was collected by filtration
  5. washwashed with hexane/ethanol (3:1)
  6. dissolutionThe obtained precipitate was dissolved in ethanol (40 mL)
  7. temperatureby heating
  8. temperaturethe mixture was naturally cooled to room temperature
  9. filtrationThe precipitated crystals were collected by filtration, ethyl acetate (20 mL)
  10. additionwas added to the mixture
  11. stirringthe mixture was stirred at 80° C.
  12. temperatureby heating
  13. temperatureAfter cooling the mixture to room temperature
  14. filtrationthe precipitate was collected by filtration
  15. washwashed with ethyl acetate
  16. customdried under reduced pressure at 100° C. for 3 hr

出典と根拠

ORDレコード
ord-a4105bddbd094c528a9358b77071238a
出典データセット
uspto-grants-2012_09
特許番号
US08273741B2

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