Hydrochloric Acid → HCID 57929870, compound

HRID 1930071Notes

Reaction equation

HRID 1930071 reaction equation
[C:1]([CH:3]([C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([CH:18]([CH3:20])[CH3:19])=[N:16][N:17]=2)[N:14]=1)C(OCC)=O)#[N:2].Cl>>[CH:18]([C:15]1[N:13]2[N:14]=[C:9]([CH2:3][C:1]#[N:2])[CH:10]=[CH:11][C:12]2=[N:17][N:16]=1)([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 57929844HCID 57929844, compound

Product 1

HCID 57929870HCID 57929870, compoundYield 58%

Conditions

Temperature
105 °C

Procedure

Ethyl 2-cyano-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)acetate (1.16 g, 4.24 mmol) was suspended in 5N HCl (15 mL, 75 mmol) then heated at about 105° C. for about 20 min. The mixture was cooled to ambient temperature then concentrated under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (25 mL) and EtOAc (50 mL). The aqueous layer was extracted with EtOAc (25 mL), the combined organics were dried over MgSO4, filtered and concentrated under reduced pressure. The oil was purified by flash chromatography on silica gel using DCM/MeOH (95:5) as an eluent to give the title compound (0.493 g, 58%): LC/MS (Table 1, Method g) Rt=1.41 min; MS m/z: 202.1 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue was partitioned between saturated aqueous NaHCO3 (25 mL) and EtOAc (50 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (25 mL)
  5. dry with materialthe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe oil was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-bef7b06a888d414881d702b375d9b40d
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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