Carbon Dioxide → HCID 69307662, compound

HRID 2117736Notes

Reaction equation

HRID 2117736 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([S:20][CH2:21]C(O)=O)[N:11]([CH3:19])[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:25]([N:32]1[CH:36]=[CH:35]N=C1)(N1C=CN=C1)=[O:26].[C:37](=[O:39])=[O:38].N[C@H:41](C([O-])=O)[CH3:42].C([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([S:20][CH2:21][C:25]([NH:32][CH2:36][CH2:35][C:37]([O:39][CH2:41][CH3:42])=[O:38])=[O:26])[N:11]([CH3:19])[C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 5460980HCID 5460980, compoundHCID 58752311HCID 58752311, compound

Product 1

HCID 69307662HCID 69307662, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(4-Fluorophenyl)-1-methyl-5-pyridin-4-yl-1H-imidazol-2-ylsulfanyl]acetic acid (2 mmol/0.688 g) is dissolved in 100 ml of absolute tetrahydrofuran (THF), carbonyldiimidazole (2 mmol/0.324 g) is added and the mixture is stirred at room temperature until the evolution of carbon dioxide has ceased. Ethyl ss-alaninate (2 mmol) is then added, and the mixture is heated under reflux for 2 h. The mixture is then poured into 400 ml of 1 N Na2CO3 solution and concentrated in a rotary evaporator. The residue is extracted 3 times with in each case 150 ml of dichloromethane/ethanol 1:1, dried over sodium sulfate and concentrated in a rotary evaporator. The residue is dissolved in a little acetone and re-precipitated using diethyl ether. The precipitate formed is filtered off with suction and dried over P2O5.

Workup

  1. additionis then added
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 2 h
  4. concentrationconcentrated in a rotary evaporator
  5. extractionThe residue is extracted 3 times with in each case 150 ml of dichloromethane/ethanol 1:1
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in a rotary evaporator
  8. dissolutionThe residue is dissolved in a little acetone
  9. customre-precipitated
  10. customThe precipitate formed
  11. filtrationis filtered off with suction
  12. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-810506c294454440a2ce2a7cd3a3d22a
Source dataset
uspto-grants-2008_10
Patent number
US07442713B2

Reaction notes

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