p-Toluenesulfonic acid → 5-(5-Chlorobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74316노트

반응식

HRID 74316 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[C:14]([CH:16]=3)[NH2:15])=[N:7][C:6]=2[CH:24]=1.[C:25]1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(OCC)(OCC)OCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]4[N:17]([CH:18]5[CH2:19][CH2:20][O:21][CH2:22][CH2:23]5)[CH:25]=[N:15][C:14]=4[CH:16]=3)=[N:7][C:6]=2[CH:24]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 674984215-Chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole

생성물 1

HCID 674985775-(5-Chlorobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole수율 973.4%

시약·촉매·용매 1

HCID 31214Ethyl orthoformate용매

반응 조건

온도
100 °C

실험 절차

To a solution of 5-chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 100-2) (300 mg, 0.873 mmol) in triethyl orthoformate (5 mL) was added p-toluenesulfonic acid (10 mg), and this was stirred at 100° C. for 2 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with chloroform. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give crude crystals that were washed with diethyl ether and ethyl acetate to yield the title compound (200 mg, 65% yield) as brown crystals.

후처리

  1. extractionthis was extracted with chloroform
  2. customThe organic layer obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude crystals that
  7. washwere washed with diethyl ether and ethyl acetate

출처 및 근거

ORD 기록
ord-09f796d2475c447cb2318cc45d917e92
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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