Propiolic Acid → HCID 22258246, compound

HRID 1610848Notes

Reaction equation

HRID 1610848 reaction equation
[C:1]([OH:5])(=O)[C:2]#[CH:3].N1(C(N2C=CN=C2)=O)C=CN=C1.[NH:18]1[C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][C:21]=2[N:20]=[C:19]1[CH2:27][C:28]([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)=[O:29]>C1COCC1>[S:31]1[CH:32]=[CH:33][CH:34]=[C:30]1[C:28]([C:27]1[CH:3]=[CH:2][C:1](=[O:5])[N:20]2[C:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=3[NH:18][C:19]=12)=[O:29]

Participants

5

Reactant 3

HCID 10110Propiolic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 22258276HCID 22258276, compound

Product 1

HCID 22258246HCID 22258246, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

126.2 mg (1.73 mmol) of propiolic acid and 336.6 mg (2.08 mmol) of 1-(1H-imidazol-1-ylcarbonyl)-1H-imidazole are dissolved in 10 ml THF. The mixture is stirred for 3 h at room temperature. To this solution 300 mg (1.15 mmol) of 2-(4,5,6,7-Tetrahydro-1H-benzimidazol-2-yl)-1-(2-thienyl)ethanone (example XII are added and the mixture is refluxed for 24 h. The solvent is evaporated under vacuum and sodium hydrogen carbonate—solution (saturated in water) is added to the crude. The solution is extracted ethyl acetate. The collected organic phases are reextracted with brine—solution an dried over sodium sulfate. The solvent is evaporated under vacuum and the crude is purified over preparative HPLC (RP18-Column, Eluent: acetonitrile-Water Gradient) to yield 150 mg (43.6% of th.) 4-(2-Thienylcarbonyl)-6,7,8,9-tetrahydropyrido[1,2-a]benzimidazol-1(5H)-one.

Workup

  1. temperaturethe mixture is refluxed for 24 h
  2. customThe solvent is evaporated under vacuum and sodium hydrogen carbonate—solution (saturated in water)
  3. additionis added to the crude
  4. extractionThe solution is extracted ethyl acetate
  5. dry with materialan dried over sodium sulfate
  6. customThe solvent is evaporated under vacuum
  7. customthe crude is purified over preparative HPLC (RP18-Column, Eluent: acetonitrile-Water Gradient)

Sources & evidence

ORD record
ord-836028362641411388411b46100ea430
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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