Triethylamine → HCID 67024431, compound

HRID 389140Notes

Reaction equation

HRID 389140 reaction equation
[S:1]([Cl:5])([CH3:4])(=[O:3])=[O:2].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([O:15][C:16]([CH3:34])([C:18]2[N:22]([CH3:23])[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:33])([F:32])[F:31])=[N:20][N:19]=2)[CH3:17])=[C:11]([CH2:13][NH2:14])[CH:12]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[ClH:5].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([O:15][C:16]([CH3:34])([C:18]2[N:22]([CH3:23])[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:31])([F:33])[F:32])=[N:20][N:19]=2)[CH3:17])=[C:11]([CH:12]=1)[CH2:13][NH:14][S:1]([CH3:4])(=[O:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 58243925HCID 58243925, compound

Product 1

HCID 67024431HCID 67024431, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of mesyl chloride (44 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 (98 μl) 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]methanesulfonamide monohydrochloride (148 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-c4e2763f752d4bd4b0ffbdbaa571809b
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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