Dichloromethane → 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 912497Notes

Reaction equation

HRID 912497 reaction equation
[NH2:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([Cl:10])=[CH:6][C:7]=1[NH:8][CH3:9].[CH2:13](Cl)Cl>C(O)(=O)C.C(OCC)(OCC)OCC.C(OCC)(=O)C>[Cl:10][C:5]1[N:4]=[C:3]([C:11]#[N:12])[C:2]2[N:1]=[CH:9][N:8]([CH3:13])[C:7]=2[CH:6]=1

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 576575713-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrile

Product 1

HCID 576575346-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
150 °C

Procedure

The suspension of 3-amino-6-chloro-4-methylamino-pyridine-2-carbonitrile (1.8 g) in DCM (5 ml), acetic acid (1.5 ml) and triethyl orthoformate (10 ml) was heated in microwave at 150° C. for 30 minutes. The mixture was then diluted with ethyl acetate (200 ml), washed with 10% sodium carbonate (100 ml), dried over sodium sulphate, solvent removed under reduced pressure, DCM (5 ml) was then added to the residue, some product crashed out and collected by filtration (0.5 g), the rest was then columned on silica gel using ethyl acetate-heptane (55:45) as eluant to give another 0.8 g of expected product (a total of 1.3 g product). 1H NMR (CDCl3) δ: 8.1 (s, 1H), 7.6 (s, 1H), 3.93 (s, 3H). MS m/z 193 (M+H).

Workup

  1. washwashed with 10% sodium carbonate (100 ml)
  2. dry with materialdried over sodium sulphate, solvent
  3. customremoved under reduced pressure, DCM (5 ml)
  4. additionwas then added to the residue
  5. filtrationcollected by filtration (0.5 g)

Sources & evidence

ORD record
ord-ca2f2ab4934a43eca62112d3a139f65c
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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