Bromocyclopentane → HCID 68432174, compound

HRID 2092073Notes

Reaction equation

HRID 2092073 reaction equation
[Br:1][C:2]1[C:3](=[O:19])[NH:4][N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18].Br[CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:19])[N:4]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:16])[CH3:17])[C@H:10]1[CH3:18]

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 68429305HCID 68429305, compound

Product 1

HCID 68432174HCID 68432174, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-5-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-3(2H)-one (30 mg, 0.092 mmol) in N,N-dimethylformamide (0.9 mL) was mixed with bromocyclopentane (20 mg, 0.138 mmol) and potassium carbonate (19 mg, 0.138 mmol) at room temperature and stirred at 80° C. overnight. After cooling, the reaction solution was concentrated, mixed with water and extracted with ethyl acetate three times. The resulting organic layer was filtered through silica gel and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform/ethyl acetate=1/1) to give the desired product (25 mg, 67% yield).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction solution was concentrated
  3. additionmixed with water
  4. extractionextracted with ethyl acetate three times
  5. filtrationThe resulting organic layer was filtered through silica gel
  6. customevaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (chloroform/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-f1a7e20b105a46f9876b75faf5200d4b
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

Loading…