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

HRID 387583ノート

反応式

HRID 387583 の反応式
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

参加物

4

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 68759898tert-butyl 4-(3-methoxy-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cc4346c5c6b34f7db5a13e4f47795f6f
出典データセット
uspto-grants-2013_02
特許番号
US08372842B2

反応ノート

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