Potassium Carbonate → N-pentyl-5-(3-phenyl-1H-1,2,4-triazol-5-yl)-1H-imidazol-4-amine

HRID 600584

반응식

HRID 600584 반응식
[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]#[N:13])[CH2:2][CH2:3][CH2:4][CH3:5].[C:14]([NH:22][NH2:23])(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.O>[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]1[NH:23][N:22]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:13]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 11955BenzoylhydrazineHCID 451205654-(pentylamino)-1H-imidazole-5-carbonitrile

생성물 1

HCID 135984693N-pentyl-5-(3-phenyl-1H-1,2,4-triazol-5-yl)-1H-imidazol-4-amine수율 17%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 962Water용매

반응 조건

온도
170 °C

실험 절차

The mixture of 4-(pentylamino)-1H-imidazole-5-carbonitrile (200 mg, 1.12 mmol), benzohydrazide (229 mg, 1.68 mmol) and potassium carbonate (100 mg, 0.72 mmol) in 1-butanol (6 ml) in a sealed tube was stirred at 170° C. for 14 hours. The reaction was diluted with water and extracted with EtOAc three times. The combined organic layers was dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by preparative LCMS (method A) to yield the desired product (50 mg, 17% yield). LCMS calculated for C16H21N6 (M+H): 297.2. found 297.1.

후처리

  1. extractionextracted with EtOAc three times
  2. dry with materialThe combined organic layers was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by preparative LCMS (method A)

출처 및 근거

ORD 기록
ord-de2fef636ebd4dc388da89a844b71e8d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902205B2

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