N-Methylcyclohexylamine → N-Cyclohexyl-N-methyl-1H-imidazo[4,5-b]pyridin-7-amine

HRID 1696232Notes

Reaction equation

HRID 1696232 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]=[CH:9][NH:10][C:3]=12.ClC1N=C2N=CNC2=CC=1.[CH3:21][NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(Cl)(Cl)Cl>[CH:23]1([N:22]([CH3:21])[C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]=[CH:9][NH:10][C:3]=23)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 54090275-Chloro-3H-imidazo[4,5-b]pyridineHCID 127823837-Chloro-1H-imidazo[4,5-b]pyridine

Product 1

HCID 67278157N-Cyclohexyl-N-methyl-1H-imidazo[4,5-b]pyridin-7-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 1:1 mixture (100 mg) of 7-chloro-1H-imidazo[4,5-b]pyridine and 5-chloro-1H-imidazo[4,5-b]pyridine was added N-methylcyclohexanamine (500 ul), and irradiated microwave at 200° C. for 2 hours. The reaction mixture was diluted with chloroform, washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography over NH-silica gel with a chloroform/EtOAc (100:1-100:5) as eluant to give N-cyclohexyl-N-methyl-1H-imidazo[4,5-b]pyridin-7-amine (54.8 mg) as a white solid.

Workup

  1. customirradiated microwave at 200° C. for 2 hours
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by flash column chromatography over NH-silica gel with a chloroform/EtOAc (100:1-100:5) as eluant

Sources & evidence

ORD record
ord-c0195a0ecfcd49f1ba67e657e682979b
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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