P-Cresol → 2-Furan-2-yl-7-p-tolyloxy-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277088Notes

Reaction equation

HRID 277088 reaction equation
Br[C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:9]=[C:10]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:4]2[CH:3]=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1>CN1CCCC1=O>[O:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:10]1[N:11]=[C:4]2[CH:3]=[C:2]([O:24][C:21]3[CH:22]=[CH:23][C:18]([CH3:17])=[CH:19][CH:20]=3)[CH:7]=[C:6]([NH2:8])[N:5]2[N:9]=1

Participants

4

Reactant 2

HCID 2879P-CresolHCID 111967207-Bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Product 1

HCID 183135532-Furan-2-yl-7-p-tolyloxy-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1 eq. 7-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine, 5 eq. p-methyl-phenol and a catalytic amount of CSCO3 in 200 μl N-methyl-pyrrolidon was heated for 2 h to 160°. The mixture was, after filtration, purified with reversed phase column chromatography eluting with an acetonitrile/water gradient yielding the title compound, MS m/e (%): 306 M+H+ (100%).

Workup

  1. additionA mixture of 1 eq
  2. filtrationafter filtration
  3. custompurified with reversed phase column chromatography
  4. washeluting with an acetonitrile/water

Sources & evidence

ORD record
ord-418cbd01ba354e26b5558168abab9448
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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