HCID 70351491, compound → HCID 70351300, compound

HRID 1032367Notes

Reaction equation

HRID 1032367 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]#[C:24][CH2:25][N:26]([CH3:28])[CH3:27])=[C:10]1[C:29]([O:31][CH2:32][CH3:33])=[O:30].[H][H]>N1C=CC=CC=1.[Pd]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][N:26]([CH3:28])[CH3:27])=[C:10]1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

5

Reactant 2

HCID 70351491HCID 70351491, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70351300HCID 70351300, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

A solution of 4-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-1-dimethylaminobut-2-yne (1.10 g) in pyridine (75 ml) was stirred at room temperature in the presence of 5% palladium on calcium carbonate under one atmosphere of hydrogen for 45 minutes. The mixture was evaporated and the residue twice taken up in toluene and evaporated. The residue was purified by chromatography on SiO2 (20 g) using dichloromethane plus 1-5% of 10% 0.880 aqueous ammonia in methanol as eluant. Appropriate fractions were combined and evaporated. The residue was dissolved in methanol (20 ml) and the solution treated with fumaric acid (74 mg). The mixture was then evaporated and the residue crystallised from ethyl acetate to give the fumarate salt of the title compound (0.195 g) as a hemihydrate, m.p. 142°-146°.

Workup

  1. customThe mixture was evaporated
  2. customevaporated
  3. customThe residue was purified by chromatography on SiO2 (20 g)
  4. customevaporated
  5. dissolutionThe residue was dissolved in methanol (20 ml)
  6. additionthe solution treated with fumaric acid (74 mg)
  7. customThe mixture was then evaporated
  8. customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record
ord-fd2d6f13590c4f0698636be2e4302344
Source dataset
uspto-grants-1990_09
Patent number
US04957930

Reaction notes

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