Hydrochloric Acid → HCID 54148594, compound

HRID 566868Notes

Reaction equation

HRID 566868 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]([CH3:27])[CH:12]=[C:13]([NH:15][C:16]([C:18]3[N:19]([CH3:26])[CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=3)=[O:17])[CH:14]=2)=[O:9])[CH:4]=[C:3]1[C:28]([NH:30][CH2:31][CH2:32][C:33]#[N:34])=[O:29].Cl.[NH2:36][OH:37]>C(O)C>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[N:11]([CH3:27])[CH:12]=[C:13]([NH:15][C:16]([C:18]3[N:19]([CH3:26])[CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=3)=[O:17])[CH:14]=2)=[O:9])[CH:4]=[C:3]1[C:28]([NH:30][CH2:31][CH2:32][C:33](=[N:36][OH:37])[NH2:34])=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 10504385HCID 10504385, compound

Product 1

HCID 54148594HCID 54148594, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.2 g of 3-[1-methyl-4-[1-methyl-4-[1-methyl-4-nitropyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionitrile (prepared as reported in J.Med.Chem 22,1296-1301,1979) was suspended in dry ethanol and the solution saturated with dry hydrogen chloride. After 24 hours at room temperature, the solvent was evaporated in vacuum and the residue treated with two equivalents of solution of hydroxylamine in dry ethanol. After 24 hours at room temperature, the solvent was evaporated in vacuum and the residue purified by flash chromatography yielding 500 mg of 3-[1-methyl-4[1-methyl-4[1-methyl-4-nitropyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidoxime which was dissolved in a mixture of methanol-dioxane-10% hydrochloric acid (4:1:1) and reduced over Pd catalyst (10% on charcoal) in hydrogen atmosphere (50 psi) in a Parr apparatus. The solution obtained after filtration of the catalyst was evaporated in vacuum, and the solid residue suspended in dry ethanol, and filtered to yield 500 mg of intermediate.

Workup

  1. customthe solvent was evaporated in vacuum
  2. waitAfter 24 hours at room temperature
  3. customthe solvent was evaporated in vacuum
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-432b8a8202a64ed69fd71a5fb85fb263
Source dataset
uspto-grants-2001_01
Patent number
US06177408B1

Reaction notes

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