4-Pentynoic acid → 5-(But-3-ynyl)-3-(2-methoxyphenyl)-1,2,4-oxadiazole

HRID 1189086Notes

Reaction equation

HRID 1189086 reaction equation
[OH:1][N:2]=[C:3]([NH2:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].[C:13](O)(=O)[CH2:14][CH2:15][C:16]#[CH:17].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>O1CCOCC1>[CH2:16]([C:17]1[O:1][N:2]=[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:10][CH3:11])[N:12]=1)[CH2:15][C:14]#[CH:13]

Participants

6

Reactant 4

HCID 224644-Pentynoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4652214N-Hydroxy-2-methoxy-benzamidine

Product 1

HCID 860867965-(But-3-ynyl)-3-(2-methoxyphenyl)-1,2,4-oxadiazoleYield 36.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

In a reactor tube, a mixture of N′-hydroxy-2-methoxybenzamidine (598 mg, 3.6 mmol), 4-pentynoic acid (350 mg, 3.6 mmol), HOBT (0.55 g, 3.6 mmol) and EDCI.HCl (1.03 g, 5.4 mmol) in dioxane (7.4 mL) was stirred at R.T for 3h. After this time the mixture was heated at 80° C. overnight in a reaction block. The mixture was concentrated and the crude product was purified by flash chromatography (Prepacked column 25 g with DCM as eluent) to afford 299 mg of 5-(but-3-ynyl)-3-(2-methoxyphenyl)-1,2,4-oxadiazole (36%) as yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude product was purified by flash chromatography (Prepacked column 25 g with DCM as eluent)

Sources & evidence

ORD record
ord-b058cc6385f9447e8399db8ba04c4fa0
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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