Diisopropylethylamine → (3-Phenyl-1-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)methanol

HRID 1621161Notes

Reaction equation

HRID 1621161 reaction equation
Cl.Cl.[NH:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[NH2:4].C(N(CC)C(C)C)(C)C.[C:20]1([C:26]2[O:27][CH2:28][C:29](=O)[N:30]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[C:20]1([C:26]2[N:30]=[C:29]([CH2:28][OH:27])[N:3]([C:5]3[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=3)[N:4]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 69174032-Phenyloxazol-4(5H)-oneHCID 171324893-Hydrazinylpyridine dihydrochloride

Product 1

HCID 71279193(3-Phenyl-1-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-hydrazinylpyridine dihydrochloride (336 mg, 1.84 mmol) and N,N-diisopropylethylamine (476 mg, 644 μL, 3.69 mmol) in ethanol (7 mL) was added 2-phenyloxazol-4(5H)-one (300 mg, 1.68 mmol, example 55, step 1) and the reaction mixture was refluxed for 2 h. All volatiles were removed in vacuo, and the product was obtained after purification by flash chromatography (using silica gel and a methanol/ethyl acetate gradient) as light yellow solid (390 mg, 1.546 mmol, 92.3%).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. customAll volatiles were removed in vacuo
  3. customthe product was obtained
  4. customafter purification by flash chromatography (

Sources & evidence

ORD record
ord-a11e4dbe4e534dbb91ed40350df0d7dd
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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