HCID 18917508, compound → HCID 18917500, compound

HRID 1735265Notes

Reaction equation

HRID 1735265 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:34])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[N+:31]([O-])=O)=[N:21][CH:22]=3)=[O:16])[CH2:6][C:5]=12.[H][H]>C(O)C.[Pd]>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:34])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[NH2:31])=[N:21][CH:22]=3)=[O:16])[CH2:6][C:5]=12

Participants

5

Reactant 2

HCID 18917508HCID 18917508, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18917500HCID 18917500, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A room temperature solution of 1.0 g of N-[5-(5H-pyrrolo[2, 1-c][1, 4]benzodiazepin-10(11H) -ylcarbonyl)-2-pyridinyl]-2-nitrobenzamide in 100 ml of ethyl alcohol is hydrogenated over 200 mg of 10% Pd/C in a Parr apparatus under 40 psi of hydrogen for 2 hours. The reaction mixture is filtered through diatomaceous earth and the cake washed with additional ethyl alcohol. The combined filtrates are concentrated in vacuo and the residue purified by crystallization from 2:1 ethyl acetate:hexane to give the desired product as pale yellow crystals: M+Na 445:M+ 423.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. washthe cake washed with additional ethyl alcohol
  3. concentrationThe combined filtrates are concentrated in vacuo
  4. customthe residue purified by crystallization from 2:1 ethyl acetate

Sources & evidence

ORD record
ord-a36b6ebde35541928107813c75b5abf3
Source dataset
uspto-grants-1996_07
Patent number
US05536718

Reaction notes

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