Potassium hydroxy sulfite → HCID 68291300, compound

HRID 1507956Notes

Reaction equation

HRID 1507956 reaction equation
[OH:1]OS([O-])=O.[K+].[CH2:7]([S:9][C:10]1[C:11]2[N:12]([CH:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:21]=2)[N:13]=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])[CH3:8]>O.CC(C)=O>[CH2:7]([S:9]([C:10]1[C:11]2[N:12]([CH:19]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:21]=2)[N:13]=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])=[O:1])[CH3:8]

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 68291675HCID 68291675, compound

Product 1

HCID 68291300HCID 68291300, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Oxone (4139 mg, 6.73 mmol) as a solution in water (volume: 40.0 mL) was added to a stirred suspension of 4-(ethylthio)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide (910 mg, 3.06 mmol) in acetone (volume: 40 mL) at rt. The reaction mixture was stirred at rt for 3 hr. After the reaction mixture was diluted with water (5 ml), the acetone was removed by rotovap and the resulting suspension was filtered and the filter cake was washed with water. Drying afforded the title compound (890 mg, 2.84 mmol, 93% yield) as a yellow solid. The material was used as is in the next step. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34 (t, J=7.5 Hz, 3 H) 3.31-3.39 (m, 2 H) 7.31 (t, J=7.4 Hz, 1 H) 7.40-7.48 (m, 2 H) 7.74 (s, 1 H) 7.80 (d, J=7.3 Hz, 2 H) 7.98 (d, J=1.7 Hz, 1 H) 8.19-8.30 (m, 1 H) 8.49 (s, 1 H) 8.67 (d, J=1.8 Hz, 1 H).

Workup

  1. customthe acetone was removed by rotovap
  2. filtrationthe resulting suspension was filtered
  3. washthe filter cake was washed with water
  4. customDrying

Sources & evidence

ORD record
ord-f4ecd2a8cc4b4736a4c07ac96f50a3fe
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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