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Triethylamine → 2-Cyclopropyl-7-[(3S)-3-(methylamino)pyrrolidin-1-yl]-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17340
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HRID 17340 반응식
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:21]#[N:22])[C:10]([CH3:20])=[C:11]([C:14]4[N:15]=[C:16]([CH3:19])[S:17][CH:18]=4)[C:12]=3F)[N:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:30][NH:31][C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1.C(OCC)(=O)C>CS(C)=O.O>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:21]#[N:22])[C:10]([CH3:20])=[C:11]([C:14]4[N:15]=[C:16]([CH3:19])[S:17][CH:18]=4)[C:12]=3[N:34]3[CH2:35][CH2:36][C@H:32]([NH:31][CH3:30])[CH2:33]3)[N:8]=2)[CH2:3][CH2:2]1
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참가 물질

7

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HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10261057(3S)-(-)-3-(Methylamino)pyrrolidineHCID 685848052-Cyclopropyl-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685848772-Cyclopropyl-7-[(3S)-3-(methylamino)pyrrolidin-1-yl]-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile수율 17.5%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
90 °C

실험 절차

2-Cyclopropyl-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile (I-80) (100 mg, 0.32 mmol) was dissolved in dimethyl sulfoxide (2 ml), triethylamine (112 μl, 0.80 mmol) and (3S)-3-methylaminopyrrolidine (44 μl, 0.42 mmol) were added, followed by stirring at 90° C. for 6 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to preparative thin-layer silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (10:1, v/v) followed by recrystallization and purification with a mixed solvent of diethyl ether/ethyl acetate/n-hexane to obtain the entitled compound (22 mg, 17%) as a white solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated away
  5. washeluted with a mixed solvent of chloroform/methanol (10:1
  6. customv/v) followed by recrystallization and purification with a mixed solvent of diethyl ether/ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-8e91639c1fcc4e6c8f63a502696c87a4
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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