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Ethanol → 4-(5-Amino-1-benzenesulfonyl 1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1257593
ノート
印刷プレビュー

反応式

HRID 1257593 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([N+:21]([O-])=O)=[CH:19][N:18]=[C:17]3[N:24]([S:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)(=[O:29])=[O:28])[CH:25]=[CH:26][C:16]=23)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.C(O)C.CCOCC>[Pd].C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[C:20]([NH2:21])=[CH:19][N:18]=[C:17]3[N:24]([S:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)(=[O:28])=[O:29])[CH:25]=[CH:26][C:16]=23)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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

7

反応物 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 673440274-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 673232814-(5-Amino-1-benzenesulfonyl 1H-pyrrolo[2,3-b]pyridine-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester収率 69%

試薬・触媒・溶媒

2
HCID 23938Palladium触媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

A suspension of 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (11.2 g, 22.4 mmol) and palladium on carbon (1.45 g, 10%, wet, Degussa, E101 NE/W) in a 2:1 mixture of THF and ethanol (150 ml) was stirred under a hydrogen atmosphere (2-3 balloons) at 50° C. for 18 h. The reaction mixture was cooled to 25° C. then was filtered through Celite. The filtrate was concentrated under reduced pressure and the red-orange residue was purified by column chromatography on silica gel (gradient: 0 to 7% CH3OH in CH2Cl2) to give a dark red oil. This material was dissolved in CH2Cl2 (40 ml) and Et2O (200 ml) was added. Concentration of this mixture to approximately 60 ml volume under reduced pressure afforded a pink solid. This material was collected by vacuum filtration, was washed with Et2O (2×30 ml), and was air-dried to afford 4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (7.23 g, 69%). LCMS (Method G, ESI): RT=0.87 min, m+H=472.3; 1H NMR (400 MHz, DMSO) δ 8.04-7.99 (m, 2H), 7.70-7.65 (m, 1H), 7.61-7.55 (m, 3H), 7.49 (d, J=4.2 Hz, 1H), 6.78 (d, J=4.3 Hz, 1H), 5.11 (d, J=8.7 Hz, 1H), 4.37 (s, 1H), 3.94-3.86 (m, 2H), 2.95 (s, 1H), 2.54-2.48 (m, 2H), 1.92-1.79 (m, 3H), 1.40 (s, 9H), 1.38-1.27 (m, 2H).

後処理

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. filtrationthen was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe red-orange residue was purified by column chromatography on silica gel (gradient: 0 to 7% CH3OH in CH2Cl2)
  5. customto give a dark red oil
  6. customConcentration of this mixture to approximately 60 ml volume under reduced pressure afforded a pink solid
  7. filtrationThis material was collected by vacuum filtration
  8. washwas washed with Et2O (2×30 ml)
  9. customwas air-dried

出典と根拠

ORDレコード
ord-ef9380a15f46479b868c15c369f76a8b
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08461328B2

反応ノート

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