5,6-Dimethoxy-2-(4-nitro-1,2-dihydro-3H-pyrazol-3-ylidene)-2H-benzimidazole → HCID 178486794、化合物

HRID 1622410ノート

反応式

HRID 1622410 の反応式
[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][C:6]2[NH:7][C:8]([C:10]3[C:14]([N+:15]([O-])=O)=[CH:13][NH:12][N:11]=3)=[N:9][C:5]=2[CH:4]=1>[Pd].C(O)C.CN(C=O)C>[CH3:21][O:20][C:19]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[NH:9][C:8]([C:10]3[C:14]([NH2:15])=[CH:13][NH:12][N:11]=3)=[N:7][C:6]=2[CH:18]=1

参加物

5

反応物 1

HCID 1784867955,6-Dimethoxy-2-(4-nitro-1,2-dihydro-3H-pyrazol-3-ylidene)-2H-benzimidazole

生成物 1

HCID 178486794HCID 178486794、化合物収率 53%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5,6-dimethoxy-2-(4-nitro-1H-pyrazol-3-yl)-1H-benzimidazole (2.08 g, 7.2 mmol) and 10% palladium on carbon (200 mg) in ethanol (150 ml) and DMF (50 ml) was hydrogenated at room temperature and pressure overnight. The reaction mixture was filtered through Celite and the solvent removed in vacuo. The resulting solid was azeotroped with methanol and toluene and the solvent removed in vacuo. The crude material was purified by flash chromatography, eluting with DCM:MeOII:acetic acid:water (120:18:3:2) [DMAW120] followed by DCM:MeOH:acetic acid:water (90:18:3:2) (DMAW90). Product fractions were combined and the solvent removed in vacuo to yield 3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (˜Ig, 53%).

後処理

  1. customwas hydrogenated at room temperature
  2. custompressure overnight
  3. filtrationThe reaction mixture was filtered through Celite
  4. customthe solvent removed in vacuo
  5. customThe resulting solid was azeotroped with methanol and toluene
  6. customthe solvent removed in vacuo
  7. customThe crude material was purified by flash chromatography
  8. washeluting with DCM
  9. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-06d1d1bb7a7b42fd9dc61e629beade24
出典データセット
uspto-grants-2014_07
特許番号
US08778936B2

反応ノート

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