Bistrimethylsilylacetamid → HCID 86742171, compound

HRID 1252635Notes

Reaction equation

HRID 1252635 reaction equation
[O:1]=[C:2]1[C:7]([O:8]CC2C=CC=CC=2)=[CH:6][NH:5][C:4]([C:16]([NH:18][N:19]2[CH2:23][CH2:22][N:21]([C:24]([NH:26][NH2:27])=[O:25])[C:20]2=[O:28])=[O:17])=[CH:3]1.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[H][H]>C(#N)C.[Pd]>[OH:8][C:7]1[C:2](=[O:1])[CH:3]=[C:4]([C:16]([NH:18][N:19]2[CH2:23][CH2:22][N:21]([C:24]([NH:26][NH2:27])=[O:25])[C:20]2=[O:28])=[O:17])[NH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11708267BistrimethylsilylacetamidHCID 86742172HCID 86742172, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86742171HCID 86742171, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

3-[[[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2pyridinyl]carbonyl]amino]-2-oxo-1-imidazolidinecarboxylic acid, hydrazide (21.9 g) was suspended in 250 ml of acetonitrile. To the suspension was added 75 ml of bis-trimethylsilylacetamide and the mixture was stirred to form a solution. To the solution was added 10 g of palladium on charcoal (10%) and hydrogen was passed through the vigorously stirred mixture. The debenzylation was complete after 1 hour. After filtration, 15 ml of methanol and 10 drops of acetic acid were added to precipitate the title compound. Yield: 10.8 g. This crude material was stirred with 150 ml of ethanol to yield 8.8 g of the title compound, melting point <205° C., dec.

Workup

  1. customto form a solution
  2. filtrationAfter filtration, 15 ml of methanol and 10 drops of acetic acid
  3. additionwere added
  4. customto precipitate the title compound
  5. stirringThis crude material was stirred with 150 ml of ethanol

Sources & evidence

ORD record
ord-178b80c43f414215954a1d73a12c8673
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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