Potassium Carbonate → HCID 78992995, compound

HRID 1504595Notes

Reaction equation

HRID 1504595 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH:11]1[CH2:14][CH:13]([OH:15])[CH2:12]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:15][CH:13]1[CH2:14][N:11]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 804566-ChloronicotinamideHCID 15142903-Hydroxyazetidine

Product 1

HCID 78992995HCID 78992995, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 6-chloronicotinamide (0.16 g, 1 mmol) and azetidin-3-ol (73 mg, 1 mmol) in DMF (5 ml) under nitrogen was added K2CO3 (0.41 g, 3 mmol). The resulting solution was stirred under nitrogen at 125° C. for 24 h. After all the starting materials were consumed, the reaction mixture was allowed to cool to ambient temperature. The reaction mixture was then filtered and the filter cake was washed with ethyl acetate. The combined filtrates were concentrated to afford the title compound (50 mg, 25%) as a yellow solid. [LCMS RtA=0.81 min, [M+H]+=194.1].

Workup

  1. customAfter all the starting materials were consumed
  2. temperatureto cool to ambient temperature
  3. filtrationThe reaction mixture was then filtered
  4. washthe filter cake was washed with ethyl acetate
  5. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-df7dc700cbb94f0fae475e32b9162eb5
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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