Ethyl Acetate → 5-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74187

반응식

HRID 74187 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].[CH:24](OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=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)[CH:24]=[N:15][C:14]=2[CH:16]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

생성물 1

HCID 674977225-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole수율 31.5%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.20 g, 0.646 mmol), triethyl orthoformate (5 mL) was added a catalytic amount of p-toluenesulfonic acid monohydrate, and this was heated to 100° C. for 1.5 hours. The reaction mixture was cooled, ethyl acetate and water added, and this was extracted. This was washed with water, dried over magnesium sulfate, and after concentration the precipitated crystals were filtered off. These were washed with a hexane/ethyl acetate mixture solution, and dried to yield the title compound (65 mg, 31.5% yield) as light reddish-brown crystals.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionthis was extracted
  3. washThis was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationafter concentration the precipitated crystals
  6. filtrationwere filtered off
  7. washThese were washed with a hexane/ethyl acetate mixture solution
  8. customdried

출처 및 근거

ORD 기록
ord-7fb7c65b3cb14bfebba4c88cb89f09ce
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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