Sodium Hydroxide → HCID 68431485, compound

HRID 2092077Notes

Reaction equation

HRID 2092077 reaction equation
Br[C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([O:12]CC)=[O:11])[N:5]=[CH:4][C:3]=1[NH:15][C@@H:16]1[CH2:21][C@@H:20]2[CH2:22][C@@H:18]([C:19]2([CH3:24])[CH3:23])[C@H:17]1[CH3:25].[CH3:26][S-:27].[Na+].O1CCOCC1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:26][S:27][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([OH:12])=[O:11])[N:5]=[CH:4][C:3]=1[NH:15][C@@H:16]1[CH2:21][C@@H:20]2[CH2:22][C@@H:18]([C:19]2([CH3:24])[CH3:23])[C@H:17]1[CH3:25]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 4378561Sodium methanethiolateHCID 68431289HCID 68431289, compound

Product 1

HCID 68431485HCID 68431485, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Ethyl 2-{5-bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}acetate (220 mg, 0.533 mmol) and sodium thiomethoxide (112 mg, 1.60 mmol) in toluene (22 mL) were stirred at 80° C. for 3 hours. After cooling, the reaction solution was stirred with 1,4-dioxane (6 mL) and 1 M aqueous sodium hydroxide (1.59 mL) at room temperature for 4 hours. After completion of the reaction, the reaction solution was mixed with toluene and extracted with 1 M aqueous sodium hydroxide twice. The resulting aqueous layer was acidified to pH 1 with 1 M hydrochloric acid and extracted with ethyl acetate twice, and the extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure to give the desired product (169 mg, 90% yield).

Workup

  1. temperatureAfter cooling
  2. customAfter completion of the reaction
  3. extractionextracted with 1 M aqueous sodium hydroxide twice
  4. extractionextracted with ethyl acetate twice
  5. dry with materialthe extract was dried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-442657925847432da8b12d192decdf56
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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