Triethylamine → HCID 22611650、化合物

HRID 1738071ノート

反応式

HRID 1738071 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29].[OH-].[Na+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[Cl:25][C:26]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:27]=1[C:28]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)=[O:29]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 118312203-(1-Methylpiperidin-4-yl)-1h-indol-5-amine

生成物 1

HCID 22611650HCID 22611650、化合物収率 68.2%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 0.804 gm (3.5 mMol) 5-amino-3-(1-methylpiperidin-4-yl)-1H-indole in 10 mL tetrahydrofuran and 5.0 mL dimethylformamide were added 0.586 mL (4.2 mMol) triethylamine followed by a solution of 0.744 gm (3.86 mMol) 2-chloro-4-fluorobenzoyl chloride in 5 mL tetrahydrofuran. After 18 hours the reaction mixture was diluted with ethyl acetate followed by 2N sodium hydroxide. The phases were separated and the aqueous extracted with ethyl acetate. The organic extracts were combined then washed sequentially with 2N sodium hydroxide, water and saturated aqueous sodium chloride. The remaining organics were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash chromatography, eluting with 100:10:1 dichloromethane:methanol:ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The residue was precipitated from ethyl acetate to give 0.921 gm (68.2%) of the title compound as a light pink powder.

後処理

  1. customThe phases were separated
  2. extractionthe aqueous extracted with ethyl acetate
  3. washThe organic extracts were combined then washed sequentially with 2N sodium hydroxide, water and saturated aqueous sodium chloride
  4. dry with materialThe remaining organics were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with 100:10:1 dichloromethane
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was precipitated from ethyl acetate

出典と根拠

ORDレコード
ord-5388602a68b947b388f46804c860cee3
出典データセット
uspto-grants-1999_10
特許番号
US05962473

反応ノート

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