Pyridine → 2-Amino-5-[1-(4-cyanophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]-6-(2-furyl)nicotinonitrile

HRID 353231노트

반응식

HRID 353231 반응식
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:7]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[NH:17][CH:16]=2)=[CH:6][C:3]=1[C:4]#[N:5].[C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)#[N:23].N1C=CC=CC=1.CN(C)C=O>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:7]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([C:27]3[CH:28]=[CH:29][C:24]([C:22]#[N:23])=[CH:25][CH:26]=3)[CH:16]=2)=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 27343264-Cyanophenylboronic acidHCID 99654582-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile

생성물 1

HCID 129921402-Amino-5-[1-(4-cyanophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]-6-(2-furyl)nicotinonitrile수율 62%

시약·촉매·용매 2

HCID 165397Cupric acetate monohydrate촉매HCID 962Water용매

실험 절차

2-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile (20 mg, 0.071 mmol), 4-cyanophenylboronic acid (35 mg, 0.24 mmol), copper acetate monohydrate (3.0 mg, 0.015 mmol), pyridine (0.015 mL, 0.19 mmol) and N,N-dimethylformamide (1.0 mL) were introduced into a reaction vessel and stirred at room temperature for 20 hours. Water was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was dried, and then dissolved in dimethyl sulfoxide (1.0 mL) and purified by high performance liquid chromatography, to give the title compound as a yellow solid (8.32 mg, 62%).

후처리

  1. extractionby extracting with ethyl acetate
  2. customThe organic layer was dried
  3. dissolutiondissolved in dimethyl sulfoxide (1.0 mL)
  4. custompurified by high performance liquid chromatography

출처 및 근거

ORD 기록
ord-7c747ebadead41eba90261d209f3ff9d
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750232B2

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