Triethylamine → HCID 71063033, compound

HRID 875472Notes

Reaction equation

HRID 875472 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([N:11]2[C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[CH:13]=[CH:12]2)=[O:10])=[C:4]([Cl:20])[CH:3]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>O1CCCC1>[Cl:8][C:6]1[CH:7]=[C:2]([NH:1][C:28](=[O:31])[CH2:29][CH3:30])[CH:3]=[C:4]([Cl:20])[C:5]=1[C:9]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[CH:13]=[CH:12]1)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 86720659HCID 86720659, compound

Product 1

HCID 71063033HCID 71063033, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4-amino-2,6-dichlorophenyl)(1H-pyrrolo[3,2-c]pyridin-1-yl)methanone (45 mg, 0.15 mmol) and triethylamine (0.04 mL, 0.29 mmol) in tetrahydrofuran (1 mL), propanoyl chloride (0.014 mL, 0.16 mmol) was added drop wise at 0° C. The resulting reaction mixture was stirred at room temperature for 30 minutes and concentrated under vacuum. The residue was diluted with water, extracted with ethyl acetate (2×20 mL). The combined organic portion was washed with brine, dried over anhydrous sodium sulphate and concentrated on rotary evaporator. The residue was taken up in methanol (2 mL), potassium carbonate (25 mg) was added and stirred at room temperature for 10 minutes, concentrated on a rotary evaporator, diluted with water (10 mL) and extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine, dried over anhydrous sodium sulphate and concentrated on rotary evaporator. N-[3,5-dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]propanamide (7.4 mg, 14%) was isolated by silica gel column chromatography using dichloromethane and methanol gradient as eluent.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under vacuum
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. washThe combined organic portion was washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated on rotary evaporator
  8. additionpotassium carbonate (25 mg) was added
  9. stirringstirred at room temperature for 10 minutes
  10. concentrationconcentrated on a rotary evaporator
  11. additiondiluted with water (10 mL)
  12. extractionextracted with ethyl acetate
  13. washThe combined organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
  14. dry with materialdried over anhydrous sodium sulphate
  15. concentrationconcentrated on rotary evaporator

Sources & evidence

ORD record
ord-afe63e802ae64a0e90291a329201ebbb
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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