Methyl iodide → 2-(4-Methoxyphenyl)-1-methyl-1H-benzimidazole-4-carboxamide

HRID 382355노트

반응식

HRID 382355 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]3[C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[OH-].[K+].[CH3:23]I>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH3:23])[C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([NH2:20])=[O:19])[C:11]=3[N:10]=2)=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178488846HCID 178488846, 화합물

생성물 1

HCID 105407722-(4-Methoxyphenyl)-1-methyl-1H-benzimidazole-4-carboxamide

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

2-(4′-Methoxyphenyl)benzimidazole-4-carboxamide (NU1076 from Example 5) (105.3 mg, 0.394 mmol) and powdered potassium hydroxide (22 mg, 0.394 mmol) were suspended in acetone (4 ml) and stirred until all the solids had dissolved. Methyl iodide (24.6 μll, 0.394 mmol) was added and the reaction stirred at room temperature overnight. The solvent was removed under reduced pressure and the white solid residue purified by column chromatography with dichloromethane/methanol 95:5 to give fine white crystals of the title compound. (33.2 mg, 30%) mp 289-292° C.; Found C 68.62 H 5.36 N 14.67 C16Hl5N3O2 Requires C 68.33 H 5.34 N 14.95; vmax(cm−1) 3309.23, 3141.44, 1671.29, 1605.30, 1255.08, δH 3.95 (3H, s), 4.02 (3H, s), 7.22-7.27 (2H, d), 7.44-7.52 (1H, t), 7.86-8.00 (5H, m), 9.4 (1H, br s, NH); m/z (EI) 281 (M+), 264, 250.

후처리

  1. dissolutionhad dissolved
  2. stirringthe reaction stirred at room temperature overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe white solid residue purified by column chromatography with dichloromethane/methanol 95:5

출처 및 근거

ORD 기록
ord-056a59c1f9a940fd87e11548b35443a8
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310082B1

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