Sodium Iodide → 6-(4-(3-acetylaminobenzoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 912529노트

반응식

HRID 912529 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8]Cl)(=[O:3])[CH3:2].[OH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:25]=[C:24]([C:26]#[N:27])[C:23]3[N:28]=[CH:29][N:30](C)[C:22]=3[CH:21]=2)=[CH:16][C:15]=1[C:32]([F:35])([F:34])[F:33].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:25]=[C:24]([C:26]#[N:27])[C:23]3[N:28]=[CH:29][NH:30][C:22]=3[CH:21]=2)=[CH:16][C:15]=1[C:32]([F:35])([F:34])[F:33])(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 18792834N-(3-(chloromethyl)phenyl)acetamideHCID 1360110856-(4-Hydroxy-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

생성물 1

HCID 468426686-(4-(3-acetylaminobenzoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

A mixture of 3-acetylaminobenzylchloride (200 mg), 6-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (350 mg), sodium iodide (16 mg) and potassium carbonate (300 mg) in acetonitrile (20 ml) was heated at 80° C. for 14 hours. After cooling to room temperature, water (30 ml) was added, the white precipitate collected by filtration was dissolved in DMSO (1 ml) and purified by HPLC to give 6-(4-(3-acetylaminobenzoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile. 1H NMR (DMSO) δ: 8.71 (s, 1H), 8.64 (s, 1H), 8.43 (m, 2H), 7.74 (s, 1H), 7.51 (m, 2H), 7.33 (t, 1H), 7.15 (d, 1H), 5.34 (s, 2H), 3.98 (s, 3H), 2.04 (s, 3H). MS m/z 466 (M+1).

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe white precipitate collected by filtration
  3. dissolutionwas dissolved in DMSO (1 ml)
  4. custompurified by HPLC

출처 및 근거

ORD 기록
ord-4ece0bebc835413abffeb38e51eed17c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026236B2

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