Triethylamine → HCID 54526059, compound

HRID 1604591Notes

Reaction equation

HRID 1604591 reaction equation
[NH2:1][C:2]1[CH:38]=[CH:37][C:5]([CH:6]=[CH:7][C:8]([NH:10][CH2:11][C:12]([N:14]([C:16]2[C:17]([Cl:36])=[C:18]([C:32]([Cl:35])=[CH:33][CH:34]=2)[CH2:19][O:20][C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]=2[N:29]=[C:28]([CH3:31])[CH:27]=[CH:26]3)[CH3:15])=[O:13])=[O:9])=[CH:4][C:3]=1[CH3:39].C(N(CC)CC)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49]>ClCCl>[Cl:36][C:17]1[C:16]([N:14]([C:12](=[O:13])[CH2:11][NH:10][C:8](=[O:9])[CH:7]=[CH:6][C:5]2[CH:37]=[CH:38][C:2]([NH:1][S:48]([CH3:47])(=[O:50])=[O:49])=[C:3]([CH3:39])[CH:4]=2)[CH3:15])=[CH:34][CH:33]=[C:32]([Cl:35])[C:18]=1[CH2:19][O:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([CH3:31])[CH:27]=[CH:26]2

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 53932501HCID 53932501, compound

Product 1

HCID 54526059HCID 54526059, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-[3-[N-(4-amino-3-methylcinnamoylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (200 mg) and triethylamine (35.9 mg) in dichloromethane was dropwise added methanesulfonyl chloride (0.03 ml) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 1 hour at the same temperature. Methanesulfonyl chloride (0.03 ml) and triethylamine (36 mg) were further added thereto, and the mixture was stirred for 1 hour at the same temperature. The solvent was removed in vacuo, and the residue was dissolved in methanol. To the solution was added 1N sodium hydroxide solution (0.5 ml), and the mixture was stirred for 3 hours at ambient temperature and concentrated. To the residue were added dichloromethane and water, the organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=15:1, V/V) to give 8-[2,6-dichloro-3-[N-(4-methanesulfonamido-3-methylcinnamoylglycyl)-N-methylamino]benzyloxy]-2-methylquinoline (185 mg) as an amorphous powder.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred for 1 hour at the same temperature
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in methanol
  5. additionTo the solution was added 1N sodium hydroxide solution (0.5 ml)
  6. stirringthe mixture was stirred for 3 hours at ambient temperature
  7. concentrationconcentrated
  8. additionTo the residue were added dichloromethane and water
  9. washthe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  10. customdried
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=15:1, V/V)

Sources & evidence

ORD record
ord-8c4d128d7d104b98bebb6d7db6e5cf49
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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