Potassium Carbonate → HCID 80345918, compound

HRID 1504592Notes

Reaction equation

HRID 1504592 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[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:16][CH:13]1[CH2:14][CH2:15][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 982104-Hydroxypyrrolidine

Product 1

HCID 80345918HCID 80345918, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 6-chloronicotinamide (0.16 g, 1 mmol) and pyrrolidin-3-ol (0.87 g, 1 mmol) in DMF (5 ml) was added K2CO3 (0.41 g, 3 mmol). The resulting solution was stirred under nitrogen at 125° C. for 24 h, and then 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 (0.145 g, 70%) as a yellow solid. [LCMS RtA=1.23 min, [M+H]+=208.1].

Workup

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

Sources & evidence

ORD record
ord-6b4d9227b5b640849eeba8515391e42f
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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