Potassium Carbonate → HCID 18704942, compound

HRID 2287469Notes

Reaction equation

HRID 2287469 reaction equation
[Cl:1][C:2]1[C:7]([N:8]([C:10](=[O:28])[CH2:11][NH:12][C:13](=[O:27])/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=2)[CH3:9])=[CH:6][CH:5]=[C:4]([Cl:29])[C:3]=1[CH2:30][OH:31].S(Cl)(C)(=O)=O.O[C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:47]=1[N:46]=[C:45]([CH3:48])[CH:44]=[C:43]2[N:49]1[CH:53]=[CH:52][N:51]=[CH:50]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O.C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([N:8]([C:10](=[O:28])[CH2:11][NH:12][C:13](=[O:27])/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=2)[CH3:9])=[CH:6][CH:5]=[C:4]([Cl:29])[C:3]=1[CH2:30][O:31][C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:47]=1[N:46]=[C:45]([CH3:48])[CH:44]=[C:43]2[N:49]1[CH:53]=[CH:52][N:51]=[CH:50]1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 184042364-(1H-Imidazol-1-yl)-2-methylquinolin-8-olHCID 18704937HCID 18704937, compound

Product 1

HCID 18704942HCID 18704942, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2,6-dichloro-3-[N-[(E)-3-(6-ethoxycarbonylpyridin-3-yl)acryloylglycyl]-N-methylamino]-1-(hydroxymethyl)benzene (150 mg) and triethylamine (60 mg) in N,N-dimethylformamide (1.5 ml) was dropwise added mesyl chloride (35.7 mg) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. To the mixture was added 8-hydroxy-4-(imidazol-1-yl)-2-methylquinoline (66.9 mg) and potassium carbonate (205 mg) at ambient temperature, and the mixture was stirred overnight at the same temperature. Water and ethyl acetate were added thereto, and the separated organic layer was washed with 1N sodium hydroxide solution and water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (chloroform-methanol) to give 8-[2,6-dichloro-3-[N-[(E)-3-(6-ethoxycarbonylpyridin-3-yl)acryloylglycyl]-N-methylamino]benzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (158 mg) as pale yellow amorphous.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at the same temperature
  3. washthe separated organic layer was washed with 1N sodium hydroxide solution and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (chloroform-methanol)

Sources & evidence

ORD record
ord-62feda68b77247c6b0e08b9af59dabdd
Source dataset
uspto-grants-2000_07
Patent number
US06083959

Reaction notes

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