Triethylamine → 7-[(3S)-3-(Dimethylamino)-1-pyrrolidinyl]-2-(3-hydroxy-3-methylazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17484ノート

反応式

HRID 17484 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]([N:11]1[CH2:14][C:13]([OH:16])([CH3:15])[CH2:12]1)=[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>CS(C)=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]([N:11]2[CH2:14][C:13]([OH:16])([CH3:15])[CH2:12]2)=[N:7]3)[CH2:36]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685846307-Fluoro-2-(3-hydroxy-3-methylazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 685850077-[(3S)-3-(Dimethylamino)-1-pyrrolidinyl]-2-(3-hydroxy-3-methylazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 11%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
150 °C

実験手順

7-Fluoro-2-(3-hydroxy-3-methylazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-193) (230 mg, 0.68 mmol) was dissolved in DMSO (5 ml), then triethylamine (195 μl, 1.36 mmol) and (3S)-3-(dimethylamino)pyrrolidine (181 μl, 1.43 mmol) were added, followed by stirring at 150° C. for 4 hours. After cooling, concentration under reduced pressure, dilution with ethyl acetate and washing with water, the organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with chloroform/methanol (10:1, v/v) gave the entitled compound (32 mg, 11%) as a white solid.

後処理

  1. temperatureAfter cooling
  2. concentrationconcentration under reduced pressure, dilution with ethyl acetate
  3. washwashing with water
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated away under reduced pressure

出典と根拠

ORDレコード
ord-f508cb8052fa41a6ba4570e357ba2f54
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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