Triethylamine → 5-(3-Iodo-imidazo[1,2-a]pyridin-7-yl)-3H-[1,3,4]oxadiazol-2-one

HRID 341221Notes

Reaction equation

HRID 341221 reaction equation
[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([NH:13][NH2:14])=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1.[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].C(N(CC)CC)C>C1COCC1>[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[O:12][C:15](=[O:16])[NH:14][N:13]=3)=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 59320945HCID 59320945, compound

Product 1

HCID 593208155-(3-Iodo-imidazo[1,2-a]pyridin-7-yl)-3H-[1,3,4]oxadiazol-2-oneYield 115.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-Iodo-imidazo[1,2-a]pyridine-7-carboxylic acid hydrazide (196 mg, 0.5 mmol) (prepared as described in Example 329 steps a-c) in THF (10 ml) was added carbonyldiimidazole (243 mg, 1.5 mmol) and triethylamine (0.35 ml, 2.5 mmol) and the reaction mixture left to stir for 3 h. The precipitate formed in the reaction was filtered off, washed with Et2O and dried to afford the desired product (189 mg). MS: [M+H]+=329.

Workup

  1. waitthe reaction mixture left
  2. customThe precipitate formed in the reaction
  3. filtrationwas filtered off
  4. washwashed with Et2O
  5. customdried

Sources & evidence

ORD record
ord-fc8cebacc3b84c0eb2ccf15424cc7e70
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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