HCID 86694205, compound → HCID 86694206, compound

HRID 707348Notes

Reaction equation

HRID 707348 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[C:23]([N+:24]([O-])=O)=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1>[Pd].CO>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 86694205HCID 86694205, compound

Product 1

HCID 86694206HCID 86694206, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N1-(1H-benzo[d]imidazol-2-yl)-N4-(3-nitropyridin-2-yl)cyclohexane-1,4-diamine (400 mg, 1.13 mmol) and palladium on activated carbon (50% by wt, 0.20 g) in methanol (10 mL) was stirred under hydrogen at 30 psi for 2 hours. The mixture was filtered through a pad of CELITE™ and the filtrate was concentrated to give N2-[4-((1H-benzo[d]imidazol-2-yl)amino)cyclohexyl)pyridine-2,3-diamine (320 mg, 0.99 mmol, 87.4% yield) which was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through a pad of CELITE™
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f188f8a8f3794e7b9a8041d98d9d28b1
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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