1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

HRID 1696224ノート

反応式

HRID 1696224 の反応式
[CH:1]1([NH:7][C:8]2[C:13]([C:14](O)=[O:15])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[N:21]1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[Cl-].[NH4+]>CN(C)C=O.C(Cl)(Cl)Cl.O>[CH:1]1([NH:7][C:8]2[C:13]([C:14]([NH2:21])=[O:15])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

8

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 672772414-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

生成物 1

HCID 672781964-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide収率 60.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (5.0 mg) in N,N-dimethylformamide (0.1 mL) were added 1-hydroxybenzotriazole (3.9 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (4.5 mg). The mixture was stirred at 60° C. for 30 minutes. To the solution was added ammonium chloride and the mixture was stirred at ambient temperature for 18 hours. To the solution were added water and chloroform and the mixture was extracted with chloroform. The extract was dried over MgSO4, filtrated and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (3 mg) as a white powder.

後処理

  1. stirringthe mixture was stirred at ambient temperature for 18 hours
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe extract was dried over MgSO4
  4. filtrationfiltrated
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10)

出典と根拠

ORDレコード
ord-ef513ab71fd34a67ae1855dee4a2c52c
出典データセット
uspto-grants-2012_04
特許番号
US08163767B2

反応ノート

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