Triethylamine → HCID 22611650, compound

HRID 1737827Notes

Reaction equation

HRID 1737827 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 22611650HCID 22611650, compoundYield 68.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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 0.536 mL (4.2 mMol) triethylamine followed by a solution of 0.714 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.

Workup

  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

Sources & evidence

ORD record
ord-4740795ff26d498eb7e14b796bbad515
Source dataset
uspto-grants-1999_10
Patent number
US05962474

Reaction notes

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