Methyl propiolate → HCID 22258252, compound

HRID 1610845Notes

Reaction equation

HRID 1610845 reaction equation
Cl.[C:2]1([C:8](=[O:19])[CH2:9][C:10]2[NH:14][C:13]3[CH2:15][CH2:16][CH2:17][CH2:18][C:12]=3[N:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[C:23](OC)(=[O:26])[C:24]#[CH:25]>CO>[C:8]([C:9]1[CH:25]=[CH:24][C:23](=[O:26])[N:11]2[C:12]3[CH2:18][CH2:17][CH2:16][CH2:15][C:13]=3[NH:14][C:10]=12)(=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13536Methyl propiolateHCID 10942334Sodium MethoxideHCID 22258222HCID 22258222, compound

Product 1

HCID 22258252HCID 22258252, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

250 mg (0.9 mmol) of the compound of Example IX are dissolved in 2 ml Methanol. 50 mg (0.925 mmol) sodium methylate are added at room temperature and the mixture is stirred for 30 min. 75.9 mg (0.9 mmol) methyl propiolate are added and the reaction mixture is stirred for 20 h at room temperature. The solvent is evaporated under vacuum and the crude is purified over preparative HPLC (RP18-Column, Eluent: Acetonitrile-Water Gradient) to yield 113 mg (43% of th.) 4-benzoyl-6,7,8,9-tetrahydropyrido[1,2-a]benzimidazol-1(5H)-one.

Workup

  1. stirringthe reaction mixture is stirred for 20 h at room temperature
  2. customThe solvent is evaporated under vacuum
  3. customthe crude is purified over preparative HPLC (RP18-Column, Eluent: Acetonitrile-Water Gradient)

Sources & evidence

ORD record
ord-7bcdde97e9c346e2b3b03dfeab436884
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

Loading…