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

HRID 74266노트

반응식

HRID 74266 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dfd5be66472846298a55e4327a71616f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

반응 노트

불러오는 중…