Pyridine → HCID 57229176, compound

HRID 1492451Notes

Reaction equation

HRID 1492451 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=NOC=2)=[CH:4][CH:3]=1.CN(C=[O:17])C.[N:18]1[CH:23]=CC=CC=1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26]>C(#N)C>[O:17]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:25](=[O:26])[O:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[CH:7][CH:6]=2)=[N:9][CH:23]=[N:18]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 821294-Nitrophenyl chloroformateHCID 18950796HCID 18950796, compound

Product 1

HCID 57229176HCID 57229176, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-aminophenyl oxadiazole (0.97 g, 0.006 mol, compound of part A) in acetonitrile (25 mL)/DMF (2 mL) and pyridine (0.50 mL, 0.48 g, 0.006 mol) under argon at 0° C. was treated with p-nitrophenyl chloroformate (1.21 g, 0.006 mol) and was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and an effort was made to partition the remaining oil between ethyl acetate and 10% citric acid, resulting in separation of a solid insoluble in either phase. The solid was collected and triturated with anhydrous ether and dried in vacuo to yield 1.67 g of the title compound, m.p. 210°-212° C. TLC, silica gel, EtOAc/hexanes (2:1), Rf =0.58; M.S. (M+H)+ at 327, M.W. 326. This compound contained minor impurities and was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto partition the remaining oil between ethyl acetate and 10% citric acid
  3. customresulting in separation of a solid insoluble in either phase
  4. customThe solid was collected
  5. customtriturated with anhydrous ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e56338b90d9a423eb7078358849c0aea
Source dataset
uspto-grants-1994_12
Patent number
US05374643

Reaction notes

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