Cyclopropanemethanol → HCID 58047550, compound

HRID 1888765Notes

Reaction equation

HRID 1888765 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.[CH:12]1([CH2:15]O)[CH2:14][CH2:13]1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:15][CH:12]2[CH2:14][CH2:13]2)=[O:9])=[C:4]([CH3:11])[CH:3]=1

Participants

7

Reactant 3

HCID 75644CyclopropanemethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 467392746-Fluoro-4-methylpyridine-3-carboxylic acid

Product 1

HCID 58047550HCID 58047550, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-fluoro-4-methylpyridine-3-carboxylic acid (4.94 g, 31.8 mmol), cyclopropylmethanol (3.78 mL, 47.8 mmol) and N,N-dimethylpyridin-4-amine (778 mg, 6.37 mmol) in DMF (30 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (6.71 g, 35.0 mmol), and the mixture was stirred for 3 days. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solution was purified by basic silica gel column chromatography (ethyl acetate). The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:1) to give the title compound (3.86 g, yield 58%).

Workup

  1. washthe mixture was washed with 10% aqueous potassium carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solution was purified by basic silica gel column chromatography (ethyl acetate)
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 3:1)

Sources & evidence

ORD record
ord-6577d60eca854312b156ee34706e0495
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

Loading…