Propiolic Acid → HCID 22258184, compound

HRID 1610883Notes

Reaction equation

HRID 1610883 reaction equation
[C:1]([OH:5])(=O)[C:2]#[CH:3].N1(C(N2C=CN=C2)=O)C=CN=C1.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26](=[O:38])[CH2:27][C:28]1[NH:32][C:31]2[CH2:33][CH2:34][CH:35]([CH3:37])[CH2:36][C:30]=2[N:29]=1>>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26]([C:27]1[CH:3]=[CH:2][C:1](=[O:5])[N:29]2[C:30]3[CH2:36][CH:35]([CH3:37])[CH2:34][CH2:33][C:31]=3[NH:32][C:28]=12)=[O:38]

Participants

4

Reactant 3

HCID 10110Propiolic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 178423475HCID 178423475, compound

Product 1

HCID 22258184HCID 22258184, compound

Procedure

The compound is prepared as described in example 11 with 138 mg (1.97 mmol) of propiolic acid, 383.6 mg (2.37 mmol) of 1-(1H-imidazol-1-ylcarbonyl)-1H-imidazole and 382 mg (1.31 mmol) of 1-(2,4-difluorophenyl)-2-(5-methyl-4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)ethanone (example LIV). The isomers are isolated after purification over preparative HPLC (Daicel Chiralpak AD, eluent: iso-hexane-ethanol v/v 60:40):

Workup

  1. customThe compound is prepared
  2. customThe isomers are isolated
  3. customafter purification over preparative HPLC (Daicel Chiralpak AD, eluent: iso-hexane-ethanol v/v 60:40)

Sources & evidence

ORD record
ord-472601f61c0341e89506075f5005a4b4
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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