Dimethylformamide dimethyl acetal → HCID 178423428, compound

HRID 1422399Notes

Reaction equation

HRID 1422399 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:5]([NH2:7])=O.COC(OC)[N:15]([CH3:17])C.C(O)(=O)C.[NH2:24]N>CN(C=O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:15]=[CH:17][NH:24][N:7]=2)[CH:8]=[C:9]([CH3:11])[N:10]=1

Participants

6

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 165591Hydrazine, acetate (1:1)HCID 595344292-Chloro-6-methylpyridine-4-carboxamide

Product 1

HCID 178423428HCID 178423428, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloro-6-methyl-isonicotinamide (1.23 g) and N,N-dimethylformamide dimethyl acetal (1.05 ml) were dissolved in dry DMF (4 ml) under inert atmosphere and the resulting solution was heated to 90° C. and stirred for 1 h. The reaction mixture was cooled to room temperature and a solution of hydrazine acetate (3.32 g) in acetic acid (8 ml) was dropwise added. The mixture was heated to 90° C. and stirred for 1 h. The solvent was removed under reduced pressure and the residue partitioned between saturated aqueous solution of NaHCO3 and EtOAc. The organic phase was separated, washed with brine, dried under Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 1/1 to 3/7) affording 2-Chloro-6-methyl-4-(1H-[1,2,4]triazol-3-yl)-pyridine (0.92 g). GC (Rt)=13.21 min (method=3A)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureThe mixture was heated to 90° C.
  3. stirringstirred for 1 h
  4. customThe solvent was removed under reduced pressure
  5. customthe residue partitioned between saturated aqueous solution of NaHCO3 and EtOAc
  6. customThe organic phase was separated
  7. washwashed with brine
  8. customdried under Na2SO4
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure
  11. customThe crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 1/1 to 3/7)

Sources & evidence

ORD record
ord-55f536309d184399ab5d5661a44892f3
Source dataset
uspto-grants-2015_01
Patent number
USRE045323E1

Reaction notes

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