Sulfuric Acid → 3-Iodo-imidazo[1,2-a]pyridine-7-carboxylic acid N'-(2,2-dimethylpropionyl) hydrazide

HRID 341218Notes

Reaction equation

HRID 341218 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(N(CC)CC)C.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24].S(=O)(=O)(O)O>C1COCC1>[CH3:24][C:23]([CH3:26])([CH3:25])[C:22]([NH:14][NH:13][C:11]([C:9]1[CH:8]=[CH:7][N:6]2[C:2]([I:1])=[CH:3][N:4]=[C:5]2[CH:10]=1)=[O:12])=[O:27]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 59320945HCID 59320945, compound

Product 1

HCID 593207903-Iodo-imidazo[1,2-a]pyridine-7-carboxylic acid N'-(2,2-dimethylpropionyl) hydrazideYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Iodo-imidazo[1,2-a]pyridine-7-carboxylic acid hydrazide (906 mg, 3 mmol) (prepared as described in 2 Step preparation of example 329) was suspended in THF (10 mL). Triethylamine (0.42 mL, 3 mmol) was added followed by pivaloyl chloride (0.37 mL, 3 mmol). The reaction was stirred for 2 h at room temperature. Concentrated sulphuric acid (0.5 mL) was added to the mixture and it was stirred 1 h further. The reaction was filtered, the solid washed with EtOAc and Et2O and dried to give 3-Iodo-imidazo[1,2-a]pyridine-7-carboxylic acid N′-(2,2-dimethylpropionyl) hydrazide (875 mg) as an off-white solid.

Workup

  1. stirringwas stirred 1 h further
  2. filtrationThe reaction was filtered
  3. washthe solid washed with EtOAc and Et2O
  4. customdried

Sources & evidence

ORD record
ord-6aae5035846043e68af58fa1e6b45889
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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