Propiolic Acid → HCID 22258165, compound

HRID 1610846Notes

Reaction equation

HRID 1610846 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:39])[CH2:27][C:28]1[NH:32][C:31]2[CH2:33][CH:34]([CH3:38])[CH2:35][CH:36]([CH3:37])[C:30]=2[N:29]=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:32]2[C:31]3[CH2:33][CH:34]([CH3:38])[CH2:35][CH:36]([CH3:37])[C:30]=3[NH:29][C:28]=12)=[O:39]

Participants

5

Reactant 3

HCID 10110Propiolic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 22258173HCID 22258173, compound

Product 1

HCID 22258165HCID 22258165, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

126.8 mg (0.78 mmol) of 1-(1H-imidazol-1-ylcarbonyl)-1H-imidazole and 45.5 mg (0.65 mmol) of propiolic acid are dissolved in 8 ml THF. The mixture is stirred for 3 h at rt. To this solution 131.7 mg (0.43 mmol) of 1-(2,4-Difluorophenyl)-2-(4,6-dimethyl-4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)ethanone (example X) are added and the mixture is stirred for 20 h at rt. The solvent is evaporated under vacuum and the crude is purified over preparative HPLC (RP18-column, eluent: acetonitrile-water-gradient. The isomers are isolated after purification over preparative HPLC (Daicel Chiralpak AD, eluent: iso-hexane-ethanol v/v 30:70):

Workup

  1. stirringthe mixture is stirred for 20 h at rt
  2. customThe solvent is evaporated under vacuum
  3. customthe crude is purified over preparative HPLC (RP18-column, eluent
  4. customThe isomers are isolated
  5. customafter purification over preparative HPLC (Daicel Chiralpak AD, eluent: iso-hexane-ethanol v/v 30:70)

Sources & evidence

ORD record
ord-f7e3cea6d4d44a81ab3b3e4b0d4b447c
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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