Triethylamine → HCID 10114267, compound

HRID 547692Notes

Reaction equation

HRID 547692 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[C:17](=[O:35])[N:18]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=2)[CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:21]=1)#[N:9].[OH-].[Na+].[CH3:38][S:39](Cl)(=[O:41])=[O:40]>O1CCCC1>[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[C:17](=[O:35])[N:18]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][S:39]([CH3:38])(=[O:41])=[O:40])[CH:29]=2)[CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:21]=1)#[N:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 9925276HCID 9925276, compound

Product 1

HCID 10114267HCID 10114267, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.2 ml) was added to a solution of 31 mg of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-(3-aminophenyl)-1,2-dihydropyridin-2-one in 2 ml of tetrahydrofuran, 0.1 ml of methanesulfonic acid chloride was dropped thereinto with ice cooling and the mixture was stirred for 10 minutes. To this were added 2 ml of 2N sodium hydroxide, the mixture was stirred at room temperature for 5 minutes and partitioned to ethyl acetate-water, the organic layer was washed with water, dried and concentrated and the residue was purified by a silica gel column chromatography (ethyl acetate-hexane system) to give 38 mg of the title compound as a pale yellow amorphous substance.

Workup

  1. additionwas dropped
  2. stirringthe mixture was stirred at room temperature for 5 minutes
  3. custompartitioned to ethyl acetate-water
  4. washthe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified by a silica gel column chromatography (ethyl acetate-hexane system)

Sources & evidence

ORD record
ord-6098143302b24cd2bbaa3c3a2d715e43
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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