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1-(4-Methoxybenzyl)pyrrolidine-2,4-dione → tert-butyl 4-(1-(4-methoxybenzyl)-3-(1-(4-methoxybenzyl)-5-oxopyrrolidin-3-ylamino)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387544
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인쇄 미리보기

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HRID 387544 반응식
[B][B][B][B][B][B][B][B][B][B].[NH2:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:19]=2[N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[N:14]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)[N:13]=1.[CH3:49][O:50][C:51]1[CH:64]=[CH:63][C:54]([CH2:55][N:56]2[CH2:60][C:59](=O)[CH2:58][C:57]2=[O:62])=[CH:53][CH:52]=1>CO.C(Cl)Cl>[CH3:48][O:47][C:44]1[CH:43]=[CH:42][C:41]([CH2:40][N:14]2[C:15]3=[N:16][CH:17]=[C:18]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:19]([N:21]4[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]4)=[C:20]3[C:12]([NH:11][CH:59]3[CH2:58][C:57](=[O:62])[N:56]([CH2:55][C:54]4[CH:53]=[CH:52][C:51]([O:50][CH3:49])=[CH:64][CH:63]=4)[CH2:60]3)=[N:13]2)=[CH:46][CH:45]=1
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참가 물질

6

반응물 3

HCID 111953461-(4-Methoxybenzyl)pyrrolidine-2,4-dioneHCID 68735560tert-butyl 4-(3-amino-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylateHCID 178419135HCID 178419135, 화합물

생성물 1

HCID 68765517tert-butyl 4-(1-(4-methoxybenzyl)-3-(1-(4-methoxybenzyl)-5-oxopyrrolidin-3-ylamino)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate수율 71.4%

시약·촉매·용매

2
HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
48 °C

실험 절차

Decaborane (0.014 g, 0.12 mmol) was added to a solution of tert-butyl 4-(3-amino-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.20 g, 0.39 mmol) and 1-(4-methoxybenzyl)pyrrolidine-2,4-dione (0.10 g, 0.47 mmol) in MeOH (3 mL) and DCM (0.5 mL) and stirred at 48° C. (oil bath) for 20 hours. The solvent was removed. The resulting residue was dissolved in ethyl acetate (20 mL), washed with saturated NaHCO3 (10 mL), dried (sodium sulfate) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexane:ethyl acetate=1:1) to give tert-butyl 4-(1-(4-methoxybenzyl)-3-(1-(4-methoxybenzyl)-5-oxopyrrolidin-3-ylamino)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.20 g, 70%) as a solid. LCMS (APCI+) m/z 718(M+H)+.

후처리

  1. customThe solvent was removed
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (20 mL)
  3. washwashed with saturated NaHCO3 (10 mL)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-c370a9c8b237468db8ad9be786c6a0b0
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08372842B2

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