Trifluoroacetic acid → 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine

HRID 1826958

반응식

HRID 1826958 반응식
C(OC(=O)[NH:7][C:8]1[N:9]([CH3:26])[N:10]=[C:11]2[C:16]=1[CH2:15][CH2:14][CH2:13][N:12]2[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[Cl:25])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:25][C:18]1[CH:19]=[C:20]([CH3:24])[CH:21]=[C:22]([CH3:23])[C:17]=1[N:12]1[CH2:13][CH2:14][CH2:15][C:16]2=[C:8]([NH2:7])[N:9]([CH3:26])[N:10]=[C:11]12

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 23527225[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]carbamic acid tert-butyl ester

생성물 1

HCID 221362787-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine수율 85.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 0° C. solution of 287 mg of [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]carbamic acid tert-butyl ester (Example 8c) in 9 mL of dichloromethane, was added 3 mL of trifluoroacetic acid. After 15 min, the cooling bath was removed and the reaction mixture was allowed to stir and warm to room temperature during 3 h. The reaction mixture was then diluted with dichloromethane and washed with dilute aqueous sodium hydroxide. The aqueous phase was washed with additional dichloromethane, after which the combined organics were dried with magnesium sulfate and concentrated. The residue was chromatographed on silica gel eluting with a methanol/dichloromethane gradient to provide 182 mg of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine, mp 234–236° C.

후처리

  1. customthe cooling bath was removed
  2. additionThe reaction mixture was then diluted with dichloromethane
  3. washwashed with dilute aqueous sodium hydroxide
  4. washThe aqueous phase was washed with additional dichloromethane
  5. dry with materialafter which the combined organics were dried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with a methanol/dichloromethane gradient

출처 및 근거

ORD 기록
ord-8a38c1be7eb04e86a48240ba8beca25c
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053103B2

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