HCID 22724117, compound → HCID 22724078, compound

HRID 2086884Notes

Reaction equation

HRID 2086884 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N+:31]([O-])=O)=[O:23])[CH:16]=2)[C:11]2[N:34]=[CH:35][CH:36]=[CH:37][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO.O1CCOCC1>[NH2:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:24][C:22](=[O:23])[NH:21][C:17]1[CH:16]=[C:15]([N:12]2[C:13](=[O:14])[C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:9][C:10]3[CH:37]=[CH:36][CH:35]=[N:34][C:11]2=3)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 1

HCID 22724117HCID 22724117, compound

Product 1

HCID 22724078HCID 22724078, compoundYield 86.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-benzyl-4-[3-[3-(2-nitrophenyl)ureido]phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (120 mg) and 10% palladium on carbon (40 mg) in methanol (2 ml) and 1,4-dioxane (2 ml) was stirred under hydrogen (3 atm) at room temperature for 4 hours. The catalyst was removed by filtration and the solvent was evaporated. The residue was crystallized from methanol to give 4-[3-[3-(2-aminophenyl)ureido]phenyl]-2-benzyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (97 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-37223014b2434cc0a1eac51f8be64479
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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