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Isobutylamine → 2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isobutyl-amide

HRID 1677371
ノート
印刷プレビュー

反応式

HRID 1677371 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:14]=[C:15]3[C:21]([C:22]([OH:24])=O)=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH2:25]([NH2:29])[CH:26]([CH3:28])[CH3:27].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(Cl)Cl>[NH4+:14].[OH-:2].[CH2:25]([NH:29][C:22]([C:21]1[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:14]=2)[NH:19][CH:20]=1)=[O:24])[CH:26]([CH3:28])[CH3:27]
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

8

反応物 4

HCID 6558IsobutylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 595407962-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

生成物 2

HCID 14923Ammonium Hydroxide
HCID 49764442
2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isobutyl-amide
収率 109.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

A mixture of 2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (70 mg, 0.2 mmol), isobutylamine (44 μL, 0.42 mmol), 1-hydroxybenzotriazole hydrate (56 mg, 0.41 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (84 mg, 0.44 mmol) in DMF and CH2Cl2 was stirred at 70° C. overnight and partitioned between saturated NH4Cl and CH2Cl2. The aqueous layer was extracted with CH2Cl2 and the combined organic phases were washed with water, dried (Na2SO4), and concentrated. The residue was purified by preparative thin layer chromatography using 90:9.5:0.5 CH2Cl2:MeOH:concentrated aqueous NH4OH as eluant to afford 42 mg (50%) of 2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isobutyl-amide as a pale yellow powder. M+H 403.

後処理

  1. custompartitioned between saturated NH4Cl and CH2Cl2
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washthe combined organic phases were washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-a0c9b8023de347eb8a987fab0773b396
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08008298B2

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