18-Crown-6 → HCID 21942479, compound

HRID 2216809Notes

Reaction equation

HRID 2216809 reaction equation
F[C:2]1[C:3]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([F:21])[CH:14]=3)[O:10][N:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:22][N:23]([CH3:29])[CH2:24][CH2:25][CH2:26][CH2:27][O-:28].[K+].O1CCOCCOCCOCCOCCOCC1>CN(C)C=O>[CH3:22][N:23]([CH3:29])[CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:2]1[C:3]([C:8]2[N:12]=[C:11]([C:13]3[CH:14]=[C:15]([F:21])[CH:16]=[C:17]([C:19]#[N:20])[CH:18]=3)[O:10][N:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 21942621HCID 21942621, compoundHCID 23695224HCID 23695224, compound

Product 1

HCID 21942479HCID 21942479, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Alternatively, treatment of 3-(3-fluoropyrid-2-yl)-5-(3-fluoro-5-cyanophenyl)-1,2,4-oxadiazole with potassium 4-dimethylaminobutoxide in N,N-dimethylformamide with a catalytic amount of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) and heating at 110° C. affords crude product. Standard work up and purification by one or more methods, including silica gel chromatography, recystallization, trituration, and reversed-phase high-performance liquid chromatography (RP-HPLC) affords purified 3-(3-(4-dimethylaminobutoxy)-pyrid-2-yl)-5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazole.

Workup

  1. customaffords crude product
  2. customStandard work up and purification by one or more methods
  3. customaffords
  4. custompurified 3-(3-(4-dimethylaminobutoxy)-pyrid-2-yl)-5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazole

Sources & evidence

ORD record
ord-9aacb28c2f854fa8b380bb3cc8e12d08
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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