Triethylamine → HCID 68585123、化合物

HRID 17454

反応式

HRID 17454 の反応式
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:23]#[N:24])[C:10]([CH3:22])=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=4[F:21])[C:12]=3F)[N:8]=2)[CH2:3][CH2:2]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.C(=O)([O-])O.[Na+]>CS(C)=O.C(OCC)(=O)C>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:23]#[N:24])[C:10]([CH3:22])=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=4[F:21])[C:12]=3[N:36]3[CH2:37][CH2:38][C@H:34]([N:33]([CH3:39])[CH3:32])[CH2:35]3)[N:8]=2)[CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685869922-Cyclopropyl-6-(2,3-difluorophenyl)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 68585123HCID 68585123、化合物収率 85.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

2-Cyclopropyl-6-(2,3-difluorophenyl)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-177) (109 mg, 0.33 mmol) was dissolved in dimethyl sulfoxide (3 ml), then at room temperature, triethylamine (70 μl, 0.50 mmol) and (3S)-3-(dimethylamino)pyrrolidine (55 μl, 0.43 mmol) were added. The solution was stirred under nitrogen atmosphere at 90° C. for 23 hours. After cooling to room temperature, the reaction liquid 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, then the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=92:8) to obtain a roughly-purified product (119 mg, 85%) as a white solid. This was recrystallized from diisopropyl ether to obtain the entitled compound (71 mg) as a white solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction liquid
  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 preparative TLC (eluent, chloroform:methanol=92:8)

出典と根拠

ORDレコード
ord-23a7e82bfcd14cf883783352bf821214
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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