2,5-Dimethoxytetrahydrofuran → 2-Cyclopropyl-7-fluoro-5-methyl-6-(pyrrol-1-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17612

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HRID 17612 반응식
[NH2:1][C:2]1[C:3]([F:17])=[C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14].CO[CH:20]1[CH2:24][CH2:23][CH:22](OC)O1>C(O)(=O)C>[CH:9]1([C:7]2[O:8][C:4]3[C:5](=[C:12]([C:15]#[N:16])[C:13]([CH3:14])=[C:2]([N:1]4[CH:20]=[CH:24][CH:23]=[CH:22]4)[C:3]=3[F:17])[N:6]=2)[CH2:10][CH2:11]1

참가 물질

4

반응물 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 685852236-Amino-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685846202-Cyclopropyl-7-fluoro-5-methyl-6-(pyrrol-1-yl)-1,3-benzoxazole-4-carbonitrile수율 81%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

6-Amino-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-319) (29 mg, 0.13 mmol) was dissolved in acetic acid (2 ml), then at room temperature, 2,5-dimethoxytetrahydrofuran (49 μl, 0.38 mml) was added. The solution was stirred at 100° C. for 3 hours, then cooled to room temperature. The solvent was evaporated away under reduced pressure, the resulting residue was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=9:1, v/v) to obtain the entitled compound (28.5 mg, 81%) as a white solid.

후처리

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated away under reduced pressure
  3. extractionThe aqueous layer was further extracted twice with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

출처 및 근거

ORD 기록
ord-f99008e4791f4d79b81f58f093f7ff6f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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