Acetyl chloride → HCID 67024405, compound

HRID 389141Notes

Reaction equation

HRID 389141 reaction equation
[C:1]([Cl:4])(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:14][C:15]([CH3:33])([C:17]2[N:21]([CH3:22])[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:32])([F:31])[F:30])=[N:19][N:18]=2)[CH3:16])=[C:10]([CH2:12][NH2:13])[CH:11]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[ClH:4].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:14][C:15]([CH3:33])([C:17]2[N:21]([CH3:22])[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:31])([F:30])[F:32])=[N:19][N:18]=2)[CH3:16])=[C:10]([CH:11]=1)[CH2:12][NH:13][C:1](=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 58243925HCID 58243925, compound

Product 1

HCID 67024405HCID 67024405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of acetyl chloride (67 μl) in dichloromethane (1 ml) was slowly added to a solution of 1-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]methanamine (200 mg) and triethylamine (0.2 ml) in dichloromethane (4 ml), followed by stirring at room temperature for 2 hours. Saturated aqueous sodium bicarbonate was added to the reaction solution to cease the reaction, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=97:3) and dissolved in ethyl acetate, and 4M hydrogen chloride-ethyl acetate was added thereto, followed by stirring at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure and the residue was washed with diisopropylether to obtain N-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzyl]acetamide monohydrochloride (166 mg) as an amorphous.

Workup

  1. customthe reaction
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=97:3)
  7. dissolutiondissolved in ethyl acetate
  8. addition4M hydrogen chloride-ethyl acetate was added
  9. stirringby stirring at room temperature for 30 minutes
  10. concentrationThe reaction solution was concentrated under reduced pressure
  11. washthe residue was washed with diisopropylether

Sources & evidence

ORD record
ord-d501de43b19a40b8983c2e2798c66a02
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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