Formic Acid → 6-(2,4-Dichloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile

HRID 420501Notes

Reaction equation

HRID 420501 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([C:15]#[N:16])=[CH:13][C:12]([NH:17][NH2:18])=[N:11][CH:10]=1.[CH:19](O)=O>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([C:15]#[N:16])=[CH:13][C:12]2[N:11]([CH:19]=[N:18][N:17]=2)[CH:10]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 666590105-(2,4-Dichloro-phenyl)-2-hydrazino-isonicotinonitrile

Product 1

HCID 666590346-(2,4-Dichloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrileYield 86%

Procedure

A solution of the crude 5-(2,4-dichloro-phenyl)-2-hydrazino-isonicotinonitrile (520 mg) in formic acid (15 mL) was stirred and refluxed for 1 h. The reaction mixture was concentrated under vacuum, then the remaining residue was diluted in AcOEt (50 mL) and washed with a 2.0 M aqueous NaHCO3 solution (2×25 mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM→DCM/MeOH 7:3) to yield the title compound (397 mg, 1.37 mmol, 86% over 2 steps). MS: 289 [M+1]+; HPLC: AtRet=1.79; TLC: RF 0.41 (DCM/MeOH 95:5).

Workup

  1. temperaturerefluxed for 1 h
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionthe remaining residue was diluted in AcOEt (50 mL)
  4. washwashed with a 2.0 M aqueous NaHCO3 solution (2×25 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM→DCM/MeOH 7:3)

Sources & evidence

ORD record
ord-928df5845be54b8baf23aa1f204f6899
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

Loading…