Sulfuric Acid → HCID 57929919, compound

HRID 1929985Notes

Reaction equation

HRID 1929985 reaction equation
[C:1]([C:5]1[N:9]2[N:10]=[C:11]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=3[F:23])[CH:12]=[CH:13][C:8]2=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:24]S(O)(=O)=O>>[C:1]([C:5]1[N:9]2[N:10]=[C:11]([CH2:14][C:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=3[F:23])=[O:24])[CH:12]=[CH:13][C:8]2=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 57929850HCID 57929850, compound

Product 1

HCID 57929919HCID 57929919, compoundYield 99%

Conditions

Temperature
90 °C

Procedure

To a round bottom flask was added 3-tert-butyl-6-((2,4-difluorophenyl)ethynyl)-[1,2,4]triazolo[4,3-b]pyridazine (4.20 g, 13.5 mmol, Example #9, Step D) and concentrated H2SO4 (50 mL, 560 mmol). The reaction mixture was heated to about 90° C. for about 2 h. The reaction mixture was quenched with ice (500 g) and extracted with DCM (500 mL). The aqueous layer was neutralized to pH of about 7.0 with solid NaOH and additional ice (1000 g) was added to maintain a temperature of about 0-10° C. The aqueous layer was extracted with DCM (3×200 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography using MeOH/DCM (10:90) to give the title compound (4.4 g, 99%) as a solid. LC/MS (Table 1, Method a) Rt=3.20 min; MS m/z: 331.1 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with ice (500 g)
  2. extractionextracted with DCM (500 mL)
  3. additionwas added
  4. temperatureto maintain a temperature of about 0-10° C
  5. extractionThe aqueous layer was extracted with DCM (3×200 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-34aa8f9fbebd46debd0d938f432c0da2
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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