Pyridine → HCID 66978156, compound

HRID 2174359Notes

Reaction equation

HRID 2174359 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].O[NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=[NH:15].N1C=CC=CC=1>O1CCOCC1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]2[O:8][N:15]=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:24][CH:23]=4)=[CH:20][CH:21]=3)[N:13]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 801724-Cyanobenzoyl chlorideHCID 178513269HCID 178513269, compound

Product 1

HCID 66978156HCID 66978156, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4-cyanobenzoyl chloride (2.29 g, 13.8 mmol) in dioxane (10 ml) was added to a suspension of 4-(4′-(N-hydroxycarbamimidoyl)biphenyl-4-yloxy)butyric acid (3.23 g, 9.6 mmol) in dioxane (50 ml) and pyridine (2.5 ml, 31.6 mmol). The mixture was stirred at room temperature for 4 h, and then heated to 100° C. for 22 h. The mixture was concentrated to ½ of its original volume, diluted with water (100 ml), and acidified by addition of concentrated hydrochloric acid (3 ml). The product was isolated by filtration and washed with water (50 ml). The solid was suspended in MeCN (70 ml), heated to reflux, allowed to cool, filtered off, and dried under reduced pressure to yield 3.17 g (54%) of 4-(4′-{5-[4-cyanophenyl]-[1,2,4]oxadiazol-3-yl}biphenyl-4-yloxy)butyric acid as a solid.

Workup

  1. temperatureheated to 100° C. for 22 h
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water (100 ml)
  4. additionacidified by addition of concentrated hydrochloric acid (3 ml)
  5. customThe product was isolated by filtration
  6. washwashed with water (50 ml)
  7. temperatureheated
  8. temperatureto reflux
  9. temperatureto cool
  10. filtrationfiltered off
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-e960324f953f4ee6bc8a0f6d6eec4927
Source dataset
uspto-grants-2015_06
Patent number
US09061067B2

Reaction notes

Loading…