Trifluoroacetic acid → 3-methoxy-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 387583노트

반응식

HRID 387583 반응식
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:17]=2[N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[N:12](CC2C=CC(OC)=CC=2)[N:11]=1>C(Cl)Cl>[CH3:8][O:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:17]=2[N:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[NH:12][N:11]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acid2회HCID 68759898tert-butyl 4-(3-methoxy-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

생성물 1

HCID 687585923-methoxy-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine수율 118.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFA (0.5 mL) was added to tert-butyl 4-(3-methoxy-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.098 g, 0.185 mmol) in DCM (2 mL) and stirred at room temperature for 2 hours. The reaction mixture was then concentrated to dryness. The resulting residue was dissolved in TFA (2.85 mL, 37.01 mmol) and heated at 100° C. in a sealed tube for 5 hours. The reaction mixture was again concentrated to dryness. The resulting residue was dissolved in DCM (0.5 mL), followed by the addition of HCl in ether (2 mL, 2N). The resulting solid was collected by filtration to give 3-methoxy-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine (0.068 g, 96%). MS APCI (+) m/z 310.1 detected.

후처리

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. temperatureheated at 100° C. in a sealed tube for 5 hours
  3. concentrationThe reaction mixture was again concentrated to dryness
  4. dissolutionThe resulting residue was dissolved in DCM (0.5 mL)
  5. additionfollowed by the addition of HCl in ether (2 mL, 2N)
  6. filtrationThe resulting solid was collected by filtration

출처 및 근거

ORD 기록
ord-cc4346c5c6b34f7db5a13e4f47795f6f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372842B2

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