Hydrochloric Acid → 3-Methyl-2-[2-(4-amidinophenyl)ethyl]-imidazo[4,5-b]-pyridine-6-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide

HRID 2288323Notes

Reaction equation

HRID 2288323 reaction equation
[C:1]1([N:7]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8]([C:10]2[CH:11]=[C:12]3[N:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=4)[N:16]([CH3:29])[C:13]3=[N:14][CH:15]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(=O)([O-])[O-].[NH4+:42].[NH4+]>C(O)C>[C:1]1([N:7]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8]([C:10]2[CH:11]=[C:12]3[N:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([C:27](=[NH:42])[NH2:28])=[CH:25][CH:26]=4)[N:16]([CH3:29])[C:13]3=[N:14][CH:15]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 15870231HCID 15870231, compound

Product 1

HCID 158702323-Methyl-2-[2-(4-amidinophenyl)ethyl]-imidazo[4,5-b]-pyridine-6-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.8 g (3.7 mmol) of 3-methyl-2-[2-(4-cyanophenyl)ethyl]-imidazo[4,5-b]pyridine-6-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide were stirred into 100 l of ethanol saturated with hydrogen chloride for 16 hours first at 0° C. and then at room temperature until no more starting material could be detected by thin layer chromatography. Then the solvent was distilled off, the oily residue was taken up in 50 ml of absolute ethanol and mixed with 3.6 g (37 mMol) of ammonium carbonate. After 4 hours the solvent was distilled off in vacuo, the crude product obtained was purified by flash chromatography (silica gel; gradient:dichloromethane/ethanol 19:1 to 4:1) and evaporated down again. Yield: 1.6 g of beige solid (80% of theory), Rf value: 0.30 (silica gel; ethyl acetate/ethanol/ammonia=90:5:5)

Workup

  1. customat room temperature
  2. distillationThen the solvent was distilled off
  3. distillationAfter 4 hours the solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-1f1b9852104143f78d234c6afeb71d0e
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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