Triethylamine → HCID 136379936、化合物

HRID 17505

反応式

HRID 17505 の反応式
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.F[C:17]1[C:18]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:19]([CH3:35])[C:20]([C:33]#[N:34])=[C:21]2[C:25]=1[O:24][C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32])=[N:22]2>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:17]2[C:18]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[C:19]([CH3:35])[C:20]([C:33]#[N:34])=[C:21]3[C:25]=2[O:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[OH:32])=[N:22]3)[CH2:4]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 1363799317-Fluoro-2-(2-hydroxyphenyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 136379936HCID 136379936、化合物収率 24.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

(3S)-3-(Dimethylamino)pyrrolidine (100 μl, 0.79 mmol) and triethylamine (220 μl) were added to a dimethyl sulfoxide (5 ml) solution of 7-fluoro-2-(2-hydroxyphenyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-212) (204 mg, 0.59 mmol). The system was purged with nitrogen, then sealed up, and heated at 120° C. for 30 minutes. After cooling, the solvent was evaporated away under reduced pressure, then the resulting residue was dissolved in chloroform, and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure, and the resulting residue was subjected to silica gel column chromatography. Elution with a mixed solvent of chloroform/methanol (97:3, v/v) gave a main product. This was washed with a mixed solvent of isopropyl ether and ethanol, and the solid was collected by filtration to obtain the entitled compound (64 mg, 24%) as a pale yellow solid.

後処理

  1. customThe system was purged with nitrogen
  2. customsealed up
  3. temperatureAfter cooling
  4. customthe solvent was evaporated away under reduced pressure
  5. dissolutionthe resulting residue was dissolved in chloroform
  6. washwashed with water and saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated away under reduced pressure
  9. washElution with a mixed solvent of chloroform/methanol (97:3
  10. customv/v) gave a main product
  11. washThis was washed with a mixed solvent of isopropyl ether and ethanol
  12. filtrationthe solid was collected by filtration

出典と根拠

ORDレコード
ord-a863434d04ef44febea007493fc06517
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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