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

HRID 1696224노트

반응식

HRID 1696224 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ef513ab71fd34a67ae1855dee4a2c52c
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163767B2

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