Sodium Methoxide → HCID 178437428, compound

HRID 1741781Notes

Reaction equation

HRID 1741781 reaction equation
C[O-].[Na+].[CH2:4]([C:6]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[N:34](C4C=CC([N+]([O-])=O)=CC=4)[N:33]=[N:32][N:31]=3)=[CH:20][CH:19]=2)[C:9]2=[N:10][C:11]([CH3:15])=[CH:12][C:13]([CH3:14])=[C:8]2[N:7]=1)[CH3:5]>CO>[CH2:4]([C:6]1[N:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[NH:34][N:33]=[N:32][N:31]=3)=[CH:22][CH:23]=2)[C:9]2=[N:10][C:11]([CH3:15])=[CH:12][C:13]([CH3:14])=[C:8]2[N:7]=1)[CH3:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 10973451HCID 10973451, compound

Product 1

HCID 178437428HCID 178437428, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methoxide in methanol (30% w/v, 4 mL) was added to a solution of 2-ethyl-5,7-dimethyl-3-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-3H-imidazo[4,5-b]pyridine (A) (1.0 g) in methanol (20 mL) and the mixture was heated under reflux for 18 hours. The mixture was cooled to ambient temperature and solvent was removed by evaporation. The residue was dissolved in water (50 mL) and the solution was extracted with ether (2×50 mL). The aqueous layer was separated and adjusted to pH 5 with 1M citric acid solution. The product was collected by filtration and dried to give 2-ethyl-5,7-dimethyl-3-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-3H-imidazo[4,5-b]pyridine (0.6 g) as a solid, m.p. 175°-177° C. (decomposition); NMR (d6 -acetone): 1.26(t, 3H), 2.50(s, 3H), 2.53(s, 3H), 2.76(q, 2H), 5.49(s, 2H), 6.91(s, 1H), 7.07(d, 2H), 7.14(d, 2H), 7.6(m, 3H), 7.75(dd, 1H); mass spectrum (+ve fast atom bombardment (FAB), DMSO nitrobenzyl alcohol): 410(M+H)+ ; microanalysis, found C, 64.9; H, 5.6; N, 22.0%; C24H23N7.2.0H2O requires: C, 64.7; H, 6.0; N, 22.0%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customsolvent was removed by evaporation
  4. dissolutionThe residue was dissolved in water (50 mL)
  5. extractionthe solution was extracted with ether (2×50 mL)
  6. customThe aqueous layer was separated
  7. filtrationThe product was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-3021e276feaa42199bf3bab29cf11f25
Source dataset
uspto-grants-1994_08
Patent number
US05334718

Reaction notes

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