Acetic Acid → 6-Chloro-1H-imidazo[4,5-C]pyridine-4-carbonitrile

HRID 2079552Notes

Reaction equation

HRID 2079552 reaction equation
[NH2:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[NH2:8].[CH2:12](OC(OCC)OCC)C.CC(O)=O>C(Cl)Cl>[Cl:9][C:5]1[N:4]=[C:3]([C:10]#[N:11])[C:2]2[N:1]=[CH:12][NH:8][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 592183443,4-Diamino-6-chloropyridine-2-carbonitrile

Product 1

HCID 451205836-Chloro-1H-imidazo[4,5-C]pyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,4-diamino-6-chloropicolinonitrile (3.2 g), triethylorthoformate (16 ml) and AcOH (5.4 ml) was heated to 150° C. in DCM (16 ml) in a microwave for 15 minutes. Solvent was evaporated, residue was dissolved in EtOAc (250 mL) and washed with water (150 mL). Organic layer was dried over sodium sulphate. Solvent was evaporated under reduced pressure to yield 6-chloro-1H-imidazo[4,5-c]pyridine-4-carbonitrile (2.2 g).

Workup

  1. customSolvent was evaporated
  2. dissolutionresidue was dissolved in EtOAc (250 mL)
  3. washwashed with water (150 mL)
  4. dry with materialOrganic layer was dried over sodium sulphate
  5. customSolvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-43b04cbf6f794fea943b7891296d06d4
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

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