Sodium Iodide → HCID 59529564, compound

HRID 1877180Notes

Reaction equation

HRID 1877180 reaction equation
Cl[CH:2]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[O:6][C:7]=1[CH3:8].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([N:31]([CH3:39])[CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CN(C)C(=O)C.O>[CH:16]1([CH:2]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([N:31]([CH3:39])[CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[O:30])=[CH:27][CH:28]=2)[C:3]2[CH:4]=[C:5]([C:9]3[N:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=3)[O:6][C:7]=2[CH3:8])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 46941342Ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoateHCID 68512524HCID 68512524, compound

Product 1

HCID 59529564HCID 59529564, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-{4-[chloro(cyclohexyl)methyl]-5-methylfuran-2-yl}-6-methylpyridazine (107 mg), ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoate (175 mg), sodium carbonate (74 mg) and sodium iodide (210 mg) in N,N-dimethylacetamide (5 mL) was stirred at 80° C. for 8 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (30% ethyl acetate/hexane to 100% ethyl acetate/hexane). To the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (0.3 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (10 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (56 mg, 33%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (30% ethyl acetate/hexane to 100% ethyl acetate/hexane)
  6. additionTo the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (0.3 mL)
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. customThe solvent was evaporated under reduced pressure, and water (10 mL)
  9. additionwas added
  10. temperaturecooling
  11. stirringstirred for 1 hr
  12. filtrationThe resulting precipitate was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-a2d656a5b6f242c48fe2c8ea5603e816
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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