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Triethylamine → 7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-2-[2-methoxy-1,1-dimethylethyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17356
ノート
印刷プレビュー

反応式

HRID 17356 の反応式
F[C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]2[C:10]=1[O:9][C:8]([C:11]([CH3:16])([CH3:15])[CH2:12][O:13][CH3:14])=[N:7]2.C(N(CC)CC)C.[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1.C(OCC)(=O)C>CS(C)=O.O>[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][N:37]([C:2]2[C:3]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]3[C:10]=2[O:9][C:8]([C:11]([CH3:16])([CH3:15])[CH2:12][O:13][CH3:14])=[N:7]3)[CH2:36]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685855317-Fluoro-2-(2-methoxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 685859187-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-2-[2-methoxy-1,1-dimethylethyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 35%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

7-Fluoro-2-(2-methoxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-100) (40 mg, 0.12 mmol) was dissolved in dimethyl sulfoxide (0.8 ml), triethylamine (23 μl, 0.17 mmol) and (3S)-3-(dimethylamino)pyrrolidine (18 μl, 0.14 mmol) were added, followed by stirring at 90° C. for 3 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), and washed with n-hexane and ethyl acetate to obtain the entitled compound (18 mg, 35%) as a white solid.

後処理

  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. washv/v), and washed with n-hexane and ethyl acetate

出典と根拠

ORDレコード
ord-680d0e84eb3648ddb9730fdb30f70cc1
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

読み込み中…

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