HCID 53959759, compound → HCID 54485692, compound

HRID 839627Notes

Reaction equation

HRID 839627 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)=[CH:10][N:9]2[CH:24]=1)=[O:4].[H][H]>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)=[CH:10][N:9]2[CH:24]=1)=[O:4]

Participants

5

Reactant 2

HCID 53959759HCID 53959759, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54485692HCID 54485692, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 0.130 gms. of 2-(methoxycarbonylamino) 6-(p-nitrophenylthio) imidazo [1,2-a] pyridine in 30 ml. of glacial acetic acid is reduced at 40 psi. of hydrogen with 0.130 gm. of 5% palladium on carbon. When the uptake of hydrogen is complete, the catalyst is removed by filtration and the filtrate is evaporated to dryness in vacuo. The residue is stirred with saturated qqueous sodium bicarbonate and the resultant solids are collected by filtration, washed with water and dried in vacuo. The product melts 120°-175° C. Mass spectral data confirms the molecular ion of the product.

Workup

  1. additionA suspension of 0.130 gms
  2. customthe catalyst is removed by filtration
  3. customthe filtrate is evaporated to dryness in vacuo
  4. filtrationthe resultant solids are collected by filtration
  5. washwashed with water
  6. customdried in vacuo
  7. custommelts 120°-175° C

Sources & evidence

ORD record
ord-9418e7faed434f18be8e953a36b30b2d
Source dataset
uspto-grants-1978_06
Patent number
US04096264

Reaction notes

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