Potassium Carbonate → Ethyl 3-[5-(2-acetylaminopyridin-4-yl)-4-(4-fluorophenyl)-1-methyl-1H-imidazol-2-ylsulfanyl]propionate

HRID 2117739Notes

Reaction equation

HRID 2117739 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:18][C:17](=[S:19])[N:16]([CH3:20])[C:15]=2[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28](=[O:30])[CH3:29])[CH:22]=2)=[CH:10][CH:9]=1.Br[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CC(C)=O>[C:28]([NH:27][C:23]1[CH:22]=[C:21]([C:15]2[N:16]([CH3:20])[C:17]([S:19][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[N:18][C:14]=2[C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)[CH:26]=[CH:25][N:24]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 11782826N-{4-[5-(4-fluorophenyl)-3-methyl-2-thioxo-2H-imidazol-4-yl]pyridin-2-yl}acetamide

Product 1

HCID 58752321Ethyl 3-[5-(2-acetylaminopyridin-4-yl)-4-(4-fluorophenyl)-1-methyl-1H-imidazol-2-ylsulfanyl]propionate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (3.1 mmol/0.34 g) is added to undissolved N-{4-[5-(4-fluorophenyl)-3-methyl-2-thioxo-2H-imidazol-4-yl]pyridin-2-yl}acetamide (2.23 mmol/0.8 g), and the mixture is then suspended in 100 ml of absolute acetone. Ethyl 3-bromopropionate (2.3 mmol/0.422 g) are then added, and the mixture is stirred at room temperature for 24 h. The mixture is then heated under reflux for 3 h, the precipitate is filtered off and the filtrate is concentrated under reduced pressure using a rotary evaporator. The oily residue is separated on a column (mobile phase: CH2Cl2/EtOH, 9.5:0.5).

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 3 h
  3. filtrationthe precipitate is filtered off
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customa rotary evaporator
  6. customThe oily residue is separated on a column (mobile phase: CH2Cl2/EtOH, 9.5:0.5)

Sources & evidence

ORD record
ord-62681f2984f1462f9ed6fbb497dbb217
Source dataset
uspto-grants-2008_10
Patent number
US07442713B2

Reaction notes

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