1H-1,2,4-Triazole → HCID 11395197, compound

HRID 1772302Notes

Reaction equation

HRID 1772302 reaction equation
[NH:1]1C=NC=N1.P(Cl)(Cl)(Cl)=O.[N:11]1([C:19]([CH2:21][C@H:22]([CH2:35][OH:36])[O:23][CH2:24][P:25]([O:31][CH:32]([CH3:34])[CH3:33])([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])=[O:20])[CH:18]=[CH:17][C:15](=O)[NH:14][C:12]1=[O:13]>N1C=CC=CC=1>[N:11]1([C:19]([CH2:21][C@H:22]([CH2:35][OH:36])[O:23][CH2:24][P:25]([O:31][CH:32]([CH3:34])[CH3:33])([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])=[O:20])[CH:18]=[CH:17][C:15]([NH2:1])=[N:14][C:12]1=[O:13]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 11326794HCID 11326794, compound

Product 1

HCID 11395197HCID 11395197, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of 1,2,4-triazole (662 mg, 9.6 mmol) in 15 mL pyridine was added phosphorousoxychloride (223 μL, 2.4 mmol) at room temperature. The mixture was stirred for 10 minutes. Then the solution of 21 (289 mg, 0.80 mmol) was added to the mixture. The reaction mixture was stirred for 4 hours. Then ammonia gas was bubbled in to the reaction mixture for 1-3 hours and the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (CH2Cl2:MeOH=12:1) to give compound 22 (220 mg, 0.58 mmol) as a colorless foam, in 73% yield, which was characterized as follows:

Workup

  1. stirringThe reaction mixture was stirred for 4 hours
  2. customThen ammonia gas was bubbled in to the reaction mixture for 1-3 hours
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe residue was purified by column chromatography (CH2Cl2:MeOH=12:1)

Sources & evidence

ORD record
ord-3c1c0cb514c141e8ad8f14916abc080d
Source dataset
uspto-grants-2016_02
Patent number
US09249177B2

Reaction notes

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