Acetyl chloride → HCID 71618172, compound

HRID 875459Notes

Reaction equation

HRID 875459 reaction equation
[NH2:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([C:11]([C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:20])=[O:12])[C:6]=2[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29].C(OCC)(=O)C>O1CCCC1>[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[C:11]([N:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:28](=[O:30])[CH3:29])[C:7]=2[CH:8]=[CH:9]1)=[O:12]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 71061454HCID 71061454, compound

Product 1

HCID 71618172HCID 71618172, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of (4-amino-1H-pyrrolo[3,2-c]pyridin-1-yl)(2,6-dichlorophenyl) methanone (50 mg, 0.16 mmol) and triethylamine (0.05 ml, 0.32 mmol) in tetrahydrofuran (5 mL) was added acetyl chloride (0.01 ml, 0.15 mmol) drop wise and stirred at room temperature for about 1 hour. Ethyl acetate was added and washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated. The residue was taken up in methanol (5 mL), potassium carbonate (50 mg) was added and stirred for 10 minutes. The solvent was removed on a rotary evaporator at 20° C. and the residue was dissolved in dichloromethane, washed with water and brine, dried and concentrated to afford the crude product. Purification by silica gel column chromatography using ethyl acetate and dichloromethane gradient as eluent yielded N-[1-(2,6-dichlorobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]acetamide (45 mg, 81%).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. additionpotassium carbonate (50 mg) was added
  5. stirringstirred for 10 minutes
  6. customThe solvent was removed on a rotary evaporator at 20° C.
  7. dissolutionthe residue was dissolved in dichloromethane
  8. washwashed with water and brine
  9. customdried
  10. concentrationconcentrated
  11. customto afford the crude product
  12. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-733fbd13ce424795be5fd284550a3730
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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