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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
ノート
印刷プレビュー

反応式

HRID 387544 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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、化合物

生成物 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-carboxylate収率 71.4%

試薬・触媒・溶媒

2
HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
48 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-c370a9c8b237468db8ad9be786c6a0b0
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08372842B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート