HCID 178510357, compound → HCID 178510356, compound

HRID 1370107Notes

Reaction equation

HRID 1370107 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:17]([O-])=O)[C:6]([NH:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]2)=[N:7][CH:8]=1)#[N:2]>CO.O1CCOCC1.[Pd]>[NH2:17][C:5]1[C:6]([NH:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]2)=[N:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

5

Reactant 1

HCID 178510357HCID 178510357, compound

Product 1

HCID 178510356HCID 178510356, compoundYield 106.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-cyano-2-(trans-4-hydroxycyclohexylamino)-3-nitropyridine (3.35 g) in methanol (17 mL) and dioxane (17 mL) was added 10% palladium on activated carbon (383 mg) under nitrogen atmosphere. The mixture was shaken at room temperature under hydrogen atmosphere (3 atm) for 3 hours. The reaction mixture was filtered through a celite pad. The filtrate was concentrated in vacuo to give 3-amino-5-cyano-2-(trans-4-hydroxycyclohexylamino)pyridine (3.15 g) as a brown amorphous.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e238274fdd924089a136ee184f741fad
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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