2-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole → 2-Methyl-5-(6-aminobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74218ノート

反応式

HRID 74218 の反応式
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17]3[O:18][C:19]4[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:16][C:4]=2[N:3]=1.[H][H]>[Pd].CO>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17]3[O:18][C:19]4[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:16][C:4]=2[N:3]=1

参加物

5

反応物 2

HCID 674986292-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleHCID 178418361HCID 178418361、化合物

生成物 1

HCID 674987622-Methyl-5-(6-aminobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole収率 40.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

2-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 47-2) (135 mg, 0.357 mmol) was added to methanol (20 mL) containing palladium/carbon (Pd: 10%, 0.06 g), hydrogen was substituted in by successively reducing the pressure and purging with hydrogen gas 3 times, and this was stirred at room temperature for 2.5 hours. After substituting in nitrogen, the insoluble material was filtered off through a Celite layer (20 mm thickness), and this same layer was washed with methanol (20 mL, 3 times). The filtrate was combined with the wash solutions and the solvent was distilled out at reduced pressure, the residue obtained was purified by silica gel column chromatography to yield the title compound (50 mg, 40.2% yield) as brown crystals.

後処理

  1. custompurging with hydrogen gas 3 times
  2. filtrationthe insoluble material was filtered off through a Celite layer (20 mm thickness)
  3. washthis same layer was washed with methanol (20 mL, 3 times)
  4. distillationthe solvent was distilled out at reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-833e975568284f908dc7e5138b34377f
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

反応ノート

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