HCID 135706156, compound → N,N'-bis(tert-butoxycarbonyl)-N''-(3-(3-aminopyridin-2-yl)phenyl)guanidine

HRID 1059918Notes

Reaction equation

HRID 1059918 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:30]([O:29][C:27]([NH:26][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:12]=1)=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 1

HCID 135706156HCID 135706156, compound

Product 1

HCID 135710944N,N'-bis(tert-butoxycarbonyl)-N''-(3-(3-aminopyridin-2-yl)phenyl)guanidineYield 66.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of N,N′-bis(tert-butoxycarbonyl)-N″-(3-(3-nitropyridin-2-yl)phenyl)guanidine (520 mg) in ethanol (15 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 500 mg) under a hydrogen atmosphere for 24 hours. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure. The residue was triturated with ethanol, filtered, and dried to give N,N′-bis(tert-butoxycarbonyl)-N″-(3-(3-aminopyridin-2-yl)phenyl)guanidine (325 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was triturated with ethanol
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-2546768624bd4551a1d7553e7ae45f31
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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