Triethylamine → 2-Cyclopent-1-enyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17508노트

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HRID 17508 반응식
[C:1]1([C:6]2[O:7][C:8]3[C:9](=[C:11]([C:23]#[N:24])[C:12]([CH3:22])=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:14]=3F)[N:10]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.C(N(CC)CC)C.[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1>CS(C)=O>[C:1]1([C:6]2[O:7][C:8]3[C:9](=[C:11]([C:23]#[N:24])[C:12]([CH3:22])=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:14]=3[N:36]3[CH2:37][CH2:38][C@H:34]([N:33]([CH3:39])[CH3:32])[CH2:35]3)[N:10]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 68585126HCID 68585126, 화합물

생성물 1

HCID 529440762-Cyclopent-1-enyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 18%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
95 °C

실험 절차

2-(Cyclopent-1-en-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-214) (145 mg, 0.46 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (130 μl, 0.91 mmol) and (3S)-3-(dimethylamino)pyrrolidine (121 μl, 0.96 mmol) were added, followed by stirring at 95° C. for 4 hours. After cooled, this was concentrated under reduced pressure, diluted with chloroform, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. The eluate with chloroform/methanol (5:1, y/v) gave the entitled compound (34 mg, 18%) as a pale yellow amorphous substance.

후처리

  1. temperatureAfter cooled
  2. concentrationthis was concentrated under reduced pressure
  3. additiondiluted with chloroform
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure

출처 및 근거

ORD 기록
ord-1d8b10cebba949ba8ee2379a2765ebcd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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