Propanoic acid, 3-ethoxy-3-imino-, ethyl ester → 5-(Benzoxazol-2-yl)-2-(ethoxycarbonylmethyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74266ノート

反応式

HRID 74266 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].C(O[C:27](=N)[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])C.C(=O)([O-])O.[Na+]>C(O)C>[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:27]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:15][C:14]=2[CH:16]=1

参加物

5

反応物 3

HCID 75346Propanoic acid, 3-ethoxy-3-imino-, ethyl esterHCID 516892Sodium BicarbonateHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

生成物 1

HCID 867627065-(Benzoxazol-2-yl)-2-(ethoxycarbonylmethyl)-1-(tetrahydropyran-4-yl)benzimidazole収率 95.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (200 mg, 0.646 mmol) in ethanol (5 mL) was added ethyl 3-ethoxy-3-iminopropionate (190 mg, 0.969 mmol), and this was heated to reflux for 2 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with ethyl acetate. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The crystals obtained were purified by silica gel column chromatography to yield the title compound (249 mg, 95% yield) as gray crystals.

後処理

  1. temperaturethis was heated
  2. temperatureto reflux for 2 hours
  3. extractionthis was extracted with ethyl acetate
  4. customAfter the organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate, it
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customThe crystals obtained
  9. customwere purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-dfd5be66472846298a55e4327a71616f
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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