Benzimidazole → HCID 59727052, compound

HRID 1363137Notes

Reaction equation

HRID 1363137 reaction equation
ClC1C([N+]([O-])=O)=CC=C(Cl)N=1.NCC1C=NC=CC=1.Cl[C:21]1[N:26]=[C:25]([NH:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[C:24]([N+:35]([O-:37])=[O:36])=[CH:23][CH:22]=1.[N:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[NH:40][CH:39]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(N(CC)CC)C>[N:38]1([C:21]2[N:26]=[C:25]([NH:27][CH2:28][C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[C:24]([N+:35]([O-:37])=[O:36])=[CH:23][CH:22]=2)[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[CH:39]1

Participants

8

Reactant 5

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 310183-PyridinemethanamineHCID 852392,6-Dichloro-3-nitropyridineHCID 24904008HCID 24904008, compound

Product 1

HCID 59727052HCID 59727052, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,6-dichloro-3-nitropyridine (46) (0.5 g) in acetonitrile (20 mL) was cooled to 0° C. and treated with triethylamine (0.36 mL) followed by 3-(aminomethyl)pyridine (0.26 mL). The mixture was stirred for 30 minutes at 0° C. and eight hours at RT. The resulting solution, which contained the intermediate 6-chloro-3-nitro-N-(pyridin-3-ylmethyl)pyridin-2-amine (47), was transferred to a sealed tube containing benzimidazole (0.84 g) and potassium carbonate (3 g) and heated at 70° C. for 16 h. The mixture was cooled and filtered. The precipitated was washed with water and air-dried to provide 239 mg of the title compound (48).

Workup

  1. customwas transferred to a sealed tube
  2. temperatureheated at 70° C. for 16 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washThe precipitated was washed with water
  6. customair-dried

Sources & evidence

ORD record
ord-4ee2f5cf46fd4b788278fedac55fb7df
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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