Carbon Dioxide → HCID 69312753, compound

HRID 2117735Notes

Reaction equation

HRID 2117735 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(N1C=CN=C1)(N1C=CN=C1)=[O:26].C(=O)=O.N[C@H:41]([C:48]([OH:50])=[O:49])[CH2:42][C:43]1N=[CH:46][NH:45][CH:44]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([S:20][CH2:21][C:46]([N:45]3[CH2:44][CH2:43][CH2:42][CH:41]3[C:48]([OH:50])=[O:49])=[O:26])[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

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 58752311HCID 58752311, compoundHCID 178419078HCID 178419078, compound

Product 1

HCID 69312753HCID 69312753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(4-Fluorophenyl)-1-methyl-5-pyridin-4-yl-1H-imidazol-2-ylsulfanyl]acetic acid (1 mmol/0.344 g) are dissolved in 100 ml of absolute THF, carbonyldiimidazole (1 mmol/0.162 g) is added and the mixture is stirred at room temperature until the evolution of carbon dioxide has ceased. Histidine (1 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. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 h
  3. concentrationconcentrated in a rotary evaporator
  4. extractionThe residue is extracted 3 times with in each case 150 ml of dichloromethane/ethanol 1:1
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in a rotary evaporator
  7. dissolutionThe residue is dissolved in a little acetone
  8. customre-precipitated
  9. customThe precipitate formed
  10. filtrationis filtered off with suction
  11. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-b4845379b91d4115b8ca046de175f58f
Source dataset
uspto-grants-2008_10
Patent number
US07442713B2

Reaction notes

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