Tetrahydrofuran → HCID 86597474, compound

HRID 860461Notes

Reaction equation

HRID 860461 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[N:10]([C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=3)[N:11]=[C:12]([CH2:23]SC)[C:13]=2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:5]=[CH:4][N:3]=1.O[O:32][S:33]([O-:35])=O.[K+].O1CCC[CH2:38]1>O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[N:10]([C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=3)[N:11]=[C:12]([CH2:23][S:33]([CH3:38])(=[O:35])=[O:32])[C:13]=2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 86597475HCID 86597475, compound

Product 1

HCID 86597474HCID 86597474, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of ethyl 5-{4-(2-chloro-4-pyridinyl)-7-ethyl-2-[(methylthio)methyl]pyrrolo[1,2-b]pyridazin-3-yl}pentanoate (139 mg) in tetrahydrofuran (4 mL) and water (1 mL) was added oxone (287 mg) and the mixture was stirred at ambient temperature for 4 hours. The solution was diluted with water and extracted with ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate solution, sodium thiosulfate solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (10:1–1:1) to give ethyl 5-{4-(2-chloro-4-pyridinyl)-7-ethyl-2-[(methylsulfonyl)methyl]pyrrolo[1,2-b]pyridazin-3-yl}pentanoate as an yellow oil (124 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated sodium bicarbonate solution, sodium thiosulfate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of hexane and ethyl acetate (10:1–1:1)

Sources & evidence

ORD record
ord-cd71625690184cc5abc93ddad1f8cfe7
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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