Pyridine → HCID 53834776, compound

HRID 129680Notes

Reaction equation

HRID 129680 reaction equation
[CH3:1][N:2]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:3](=[O:27])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([CH:22]=[CH:23][C:24]([OH:26])=O)=[CH:6]1.C(Cl)(=O)C(Cl)=O.[NH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1.N1C=CC=CC=1>C(Cl)Cl.CN(C)C=O>[CH3:1][N:2]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:3](=[O:27])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([CH:22]=[CH:23][C:24]([N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:26])=[CH:6]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 54517660HCID 54517660, compound

Product 1

HCID 53834776HCID 53834776, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a mixture of 0.63 g (1.34 mmol) of N-methyl-N-phenethyl-2-(5-benzyloxy-3-(2-carboxyvinyl)indol-1-yl]-acetamide in 15 ml of methylene chloride, cooled to 0° C. with an external ice bath, is added dropwise 0.26 ml (3.02 mmol) of oxalyl chloride, followed immediately with 3 drops of N,N-dimethylformamide. The mixture is stirred in an ice bath for 30 minutes and then for 1 hour with the cooling bath removed. The reaction mixture is then concentrated in vacuo. The residue obtained is dissolved in 10 ml of methylene chloride and this solution is added dropwise to a mixture of 0.11 ml (1.34 mmol) of pyrrolidine, 0.24 ml of pyridine and 15 ml of methylene chloride with stirring at 0° C. (ice bath). The resulting reaction mixture is stirred at room temperature for several hours and quenched with saturated aqueous NH4Cl solution. Ethyl acetate and water are added and the layers separated. The organic layer is washed with 1N aqueous HCl solution and water, dried over magnesium sulfate and concentrated in vacuo. The residue is triturated in hot ethyl acetate to give N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-(1-pyrrolidinecarbonyl)-vinyl)indol-1-yl]acetamide (m.p. 185°-187° C.).

Workup

  1. customfor 1 hour with the cooling bath removed
  2. concentrationThe reaction mixture is then concentrated in vacuo
  3. customThe residue obtained
  4. stirringwith stirring at 0° C. (ice bath)
  5. customThe resulting reaction mixture
  6. stirringis stirred at room temperature for several hours
  7. customquenched with saturated aqueous NH4Cl solution
  8. additionEthyl acetate and water are added
  9. customthe layers separated
  10. washThe organic layer is washed with 1N aqueous HCl solution and water
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated in vacuo
  13. customThe residue is triturated in hot ethyl acetate

Sources & evidence

ORD record
ord-ec80677adc2d48c2b0bc45c80983d158
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Reaction notes

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