Isopropylamine → HCID 68432160, compound

HRID 2092072Notes

Reaction equation

HRID 2092072 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl[CH2:6][S:7](Cl)(=[O:9])=[O:8].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].[Br:24][C:25]1[C:26](=[O:42])[NH:27][N:28]=[CH:29][C:30]=1[NH:31][C@@H:32]1[CH2:37][C@@H:36]2[CH2:38][C@@H:34]([C:35]2([CH3:40])[CH3:39])[C@H:33]1[CH3:41].[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C.ClCCl>[Br:24][C:25]1[C:26](=[O:42])[N:27]([CH2:6][S:7]([NH:4][CH:1]([CH3:3])[CH3:2])(=[O:9])=[O:8])[N:28]=[CH:29][C:30]=1[NH:31][C@@H:32]1[CH2:37][C@@H:36]2[CH2:38][C@@H:34]([C:35]2([CH3:40])[CH3:39])[C@H:33]1[CH3:41]

Participants

10

Reactant 6

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 77054(Chloromethyl)sulfonyl chlorideHCID 68429305HCID 68429305, compound

Product 1

HCID 68432160HCID 68432160, compoundYield 5.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Isopropylamine (0.262 mL, 3.07 mmol), chloromethylsulfonyl chloride (0.274 mL, 3.07 mmol) and triethylamine (0.856 mL, 6.14 mmol) were added to dichloromethane (2 mL) under cooling with ice, and the resulting mixture was stirred for 2 hours under cooling with ice. After completion of the reaction, the reaction mixture was mixed with ethyl acetate, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting reaction product was dissolved in N,N-dimethylformamide (3.2 mL) and mixed with potassium carbonate (267 mg, 1.93 mmol) and 4-bromo-5-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-3(2H)-one (276 mg, 0.844 mmol) at room temperature and stirred at 80° C. for 4 hours. After cooling, the reaction solution was mixed with saturated aqueous ammonium chloride and extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform/methanol=80/1) to give the desired product (22 mg, 4% yield).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. customAfter completion of the reaction
  4. washthe organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe resulting reaction product
  8. stirringstirred at 80° C. for 4 hours
  9. temperatureAfter cooling
  10. extractionextracted with ethyl acetate
  11. washThe resulting organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customevaporated under reduced pressure
  14. customThe resulting residue was purified by silica gel chromatography (chloroform/methanol=80/1)

Sources & evidence

ORD record
ord-f73facf3493845d7bbc83c29a1a627c8
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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