1H-1,2,4-Triazole → HCID 86761458, compound

HRID 657475Notes

Reaction equation

HRID 657475 reaction equation
[NH:1]1C=NC=N1.P(Cl)(Cl)(Cl)=[O:7].[N:11]1([C:19]2([O:36][CH2:35][C@H:22]([O:23][CH2:24][P:25]([O:31][CH:32]([CH3:34])[CH3:33])([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21]2)[OH:20])[CH:18]=[CH:17][C:15](=O)[NH:14][C:12]1=[O:13]>N1C=CC=CC=1>[O:36]=[CH:35][C@H:22]([C@@H:21]([CH2:19][OH:20])[OH:7])[OH:23].[N:11]1([C:19]2([O:36][CH2:35][C@H:22]([O:23][CH2:24][P:25]([O:27][CH:28]([CH3:30])[CH3:29])([O:31][CH:32]([CH3:34])[CH3:33])=[O:26])[CH2:21]2)[OH: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 86761460HCID 86761460, compound

Product 1

HCID 86761458HCID 86761458, compoundYield 145%

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-e251a6e5c4484db69da78953b4c1e25c
Source dataset
uspto-grants-2011_12
Patent number
US08076310B2

Reaction notes

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