3-Pyridinecarboxaldehyde → 5-(Benzoxazol-2-yl)-2-(3-pyridyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74191

反応式

HRID 74191 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=1.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:30]([C:26]3[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=3)=[N:15][C:14]=2[CH:16]=1

参加物

7

反応物 4

HCID 103713-PyridinecarboxaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

生成物 1

HCID 674978935-(Benzoxazol-2-yl)-2-(3-pyridyl)-1-(tetrahydropyran-4-yl)benzimidazole収率 49.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

5-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.15 g, 0.484 mmol) was dissolved in DMF (3 mL) and water (0.1 mL), 3-pyridinecarboxaldehyde (0.06 g, 0.561 mmol) was added followed by oxone (0.19 g, 0.310 mmol), and this was stirred at room temperature for 2.5 hours. Aqueous potassium carbonate solution (0.09 g/15 mL) was added to the reaction solution. This was extracted with chloroform, washed with water, and after drying over magnesium sulfate, this was concentrated and purified by silica gel column chromatography. The crystals obtained were washed with hexane and a small amount of ethyl acetate, and dried to yield the title compound (95.0 mg, 49.5% yield) as white crystals.

後処理

  1. extractionThis was extracted with chloroform
  2. washwashed with water
  3. dry with materialafter drying over magnesium sulfate
  4. concentrationthis was concentrated
  5. custompurified by silica gel column chromatography
  6. customThe crystals obtained
  7. washwere washed with hexane
  8. dry with materiala small amount of ethyl acetate, and dried

出典と根拠

ORDレコード
ord-897d73089fb64b02b603065e4363a006
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

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