Formic Acid → HCID 15383547, compound

HRID 1940957Notes

Reaction equation

HRID 1940957 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]1([C:11]([NH:13][C:14]2[C:19]([N+:20]([O-])=O)=[C:18]([CH3:23])[CH:17]=[CH:16][N:15]=2)=O)[CH2:10][CH2:9]1.C(O)=O.C([N:29]([CH2:32][CH3:33])CC)C>>[CH:8]1([C:11]2[N:13]([CH2:7][C:1]3[CH:6]=[CH:5][C:4]([C:5]4[CH:6]=[CH:1][CH:2]=[CH:3][C:33]=4[C:32]#[N:29])=[CH:3][CH:2]=3)[C:14]3=[N:15][CH:16]=[CH:17][C:18]([CH3:23])=[C:19]3[N:20]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 1140TolueneHCID 8471TriethylamineHCID 15380885Cyclopropanecarboxamido-4-methyl-3-nitropyridine

Product 1

HCID 15383547HCID 15383547, compoundYield 83%

Procedure

Toluene (50 ml) was added to 4.0 g (9.7 mmol) of 2-[N-2'-cyanobiphenyl-4-yl)methyl]cyclopropanecarboxamido-4-methyl-3-nitropyridine, 4.5 g (97.8 mmol of formic acid 14.7 g (145.5 mmol) of triethylamine and 10% Pd--C (200 mg), followed by heating under reflux for 15 hours. After the reaction liquid was brought to room temperature and filtered to remove the catalyst, vacuum concentration was effected. Chloroform (100 ml) and water (100 ml) were added to the residue and the obtained mixture was caused liquid-liquid separation. The aqueous phase was further extracted with chloroform (50 ml) twice. The organic phases were combined, dried over anhydrous magnesium sulfate and subjected to vacuum concentration. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to give 2.9 g of 2-cyclopropyl-3-(2'-cyanobiphenyl-4-yl)methyl-7-methyl-3H-imidazo[4,5-b]pyridine (yield 83%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 15 hours
  3. customAfter the reaction liquid
  4. customwas brought to room temperature
  5. filtrationfiltered
  6. customto remove
  7. concentrationthe catalyst, vacuum concentration
  8. additionChloroform (100 ml) and water (100 ml) were added to the residue
  9. customliquid-liquid separation
  10. extractionThe aqueous phase was further extracted with chloroform (50 ml) twice
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationsubjected to vacuum concentration
  13. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d96fb5087a0b401588b5db77c9b81b7c
Source dataset
uspto-grants-1997_12
Patent number
US05700938

Reaction notes

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