Tetrahydrofuran → HCID 19763654, compound

HRID 1742223Notes

Reaction equation

HRID 1742223 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4C(NN)=O)=[CH:16][CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:30])[CH:3]=1.C([N:33]([CH2:36]C)CC)C.[C:38]([N:45]1C=CN=C1)(N1C=CN=C1)=[O:39].C1C[O:53]CC1>>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[N:45]4[N:33]=[CH:36][O:53][C:38]4=[O:39])=[CH:18][CH:19]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:30])[CH:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 67821553HCID 67821553, compound

Product 1

HCID 19763654HCID 19763654, compoundYield 81%

Procedure

To a solution of 4'-[[5,7-dimethyl-2-ethyl-3H-imidazo [4,5-b]pyridin-3-yl]methyl][1,1'-biphenyl-2-yl]carboxylic acid hydrazide (400 mg, 1 mmol) and triethylamine (130 mg, 1.3 mmol) in THF (20 mL) was added carbonyldiimidazole (275 mg, 1.7 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight and the solvent was evaporated. The residue was dissolved in water and the solution was adjusted to pH 3 by the addition of 1N HCl. The resulting precipitate was collected by filtration and dried under vacuum to give 5-[4'-[[5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3-yl]methyl][1,1'-biphenyl-2-yl]-1,3,4-oxadiazol-2[3H]-one (0.35 g, 81%) as a partial hydrate, mp 210°-212° C.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in water
  3. additionthe solution was adjusted to pH 3 by the addition of 1N HCl
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d6be5b18e17249eba2a1675bcf136244
Source dataset
uspto-grants-1994_08
Patent number
US05338737

Reaction notes

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