HCID 178510357, compound → HCID 178510356, compound

HRID 1370127Notes

Reaction equation

HRID 1370127 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[C:16]([N+:17]([O-])=O)=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=2)[CH2:4][CH2:3]1>CO.O1CCOCC1.[Pd]>[NH2:17][C:16]1[C:9]([NH:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]2)=[N:10][CH:11]=[C:12]([CH:15]=1)[C:13]#[N:14]

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

6-(trans-4-Hydroxycyclohexylamino)-5-nitronicotinonitrile (3.35 g) was dissolved in a mixture of methanol (17 ml) and 1,4-dioxane (17 ml), and 10% palladium on carbon (383 mg) was added to the solution under nitrogen atmosphere. The mixture was shaken at ambient temperature for 3 hours under hydrogen atmosphere (3 atm). The reaction mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo to give 5-amino-6-(trans-4-hydroxycyclohexylamino)nicotinonitrile (3.15 g) as a brown amorphous.

Workup

  1. additionwas added to the solution under nitrogen atmosphere
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2826074b8c7c4e788bb385659b3843be
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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