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

HRID 1667970

반응식

HRID 1667970 반응식
[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.O1CCCC1.O.[C:40]1([CH3:50])[CH:45]=[CH:44][C:43]([S:46]([OH:49])(=[O:48])=[O:47])=[CH:42][CH:41]=1>C(O)C>[C:40]1([CH3:50])[CH:41]=[CH:42][C:43]([S:46]([OH:49])(=[O:47])=[O:48])=[CH:44][CH:45]=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]([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

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrateHCID 24767979N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide

생성물 1

HCID 86630645N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide p-toluenesulfonate수율 92%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide (225 mg, 0.5 mmol) were added tetrahydrofuran (5.0 mL) and ethanol (5.0 mL), dissolved at 70° C., and p-toluenesulfonic acid monohydrate (95 mg, 0.5 mmol) was added thereto. Ethanol (15.0 mL) was further added to the mixture and insoluble material was filtered off. The filtrate was concentrated, ethyl acetate (10 mL) and ethanol (10 mL) were added thereto, and the mixture was concentrated again. Ethyl acetate (10 mL) and ethanol (1.0 mL) were added thereto, and the mixture was stood at room temperature for 6 hr. The precipitated crystals were collected by filtration, washed successively with a small amount of ethanol and diethyl ether, and dried under reduced pressure at 80° C. for 6 hr to give the title compound (285 mg, 92%) as white crystals.

후처리

  1. dissolutiondissolved at 70° C.
  2. filtrationwas filtered off
  3. concentrationThe filtrate was concentrated
  4. additionethyl acetate (10 mL) and ethanol (10 mL) were added
  5. concentrationthe mixture was concentrated again
  6. additionEthyl acetate (10 mL) and ethanol (1.0 mL) were added
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed successively with a small amount of ethanol and diethyl ether
  9. customdried under reduced pressure at 80° C. for 6 hr

출처 및 근거

ORD 기록
ord-325601b38528456d9172dea8da8dd72d
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044049B2

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