Propiolic Acid → HCID 22258309, compound

HRID 1610852Notes

Reaction equation

HRID 1610852 reaction equation
N1(C(N2C=CN=C2)=O)C=CN=C1.[C:13]([OH:17])(=O)[C:14]#[CH:15].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26](=[O:36])[CH2:27][C:28]1[NH:29][C:30]([CH3:35])=[C:31]([CH2:33][CH3:34])[N:32]=1>C1COCC1>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26]([C:27]1[CH:15]=[CH:14][C:13](=[O:17])[N:29]2[C:30]([CH3:35])=[C:31]([CH2:33][CH3:34])[NH:32][C:28]=12)=[O:36]

Participants

5

Reactant 3

HCID 10110Propiolic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 22258193HCID 22258193, compound

Product 1

HCID 22258309HCID 22258309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

552 mg (3.40 mmol) of 1-(1H-imidazol-1-ylcarbonyl)-1H-imidazole and 199 mg (2.83 mmol) of propiolic acid are dissolved in 25 ml THF. The mixture is stirred for 3 h at rt. To this solution are added 500 mg (1.89 mmol) of 1-(2,4-Difluorophenyl)-2-(4-ethyl-5-methyl-1H-imidazol-2-yl)ethanone (example XIII) and the mixture is refluxed for 24 h. The solvent is evaporated under vacuum and the crude is purified over preparative HPLC (RP18-Column, Eluent: acetonitrile-water-gradient). The regioisomers are isolated after purification over preparative HPLC (Daicel Chiralpak AD, eluent: iso-hexane-ethanol v/v 60:40).

Workup

  1. temperaturethe mixture is refluxed for 24 h
  2. customThe solvent is evaporated under vacuum
  3. customthe crude is purified over preparative HPLC (RP18-Column, Eluent: acetonitrile-water-gradient)
  4. customThe regioisomers are isolated
  5. customafter purification over preparative HPLC (Daicel Chiralpak AD, eluent: iso-hexane-ethanol v/v 60:40)

Sources & evidence

ORD record
ord-10ac8bd6ff974a02b6c71aba5f453086
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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