Pyridine → Morpholino(3-(pyridin-3-yl)-1H-pyrazol-1-yl)methanone

HRID 530298Notes

Reaction equation

HRID 530298 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[N:2]1.N1C=CC=CC=1.[N:18]1([C:24](Cl)=[O:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>O1CCCC1.CN(C1C=CN=CC=1)C>[O:21]1[CH2:22][CH2:23][N:18]([C:24]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)=[N:2]2)=[O:25])[CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 848104-Morpholinecarbonyl chlorideHCID 178420771HCID 178420771, compound

Product 1

HCID 66682852Morpholino(3-(pyridin-3-yl)-1H-pyrazol-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-(1H-pyrazol-3-yl)pyridine (0.435 g, 3 mmol) in tetrahydrofuran (15 ml) was added pyridine (0.367 ml, 4.50 mmol), DMAP (18.33 mg, 0.150 mmol). The solution was treated with 4-morpholinecarbonyl chloride (0.368 ml, 3.15 mmol). The reaction was heated to 80° C. for 20 hours. THF was removed by vacuum, the residue was partitioned between DCM and water. The organic phase was dried over MgSO4 and filtered. After evaporation the crude product was chromatographed in petroleumether:EtOAc=2:1. (Yield: 174 mg, 21%).

Workup

  1. customTHF was removed by vacuum
  2. customthe residue was partitioned between DCM and water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customAfter evaporation the crude product
  6. customwas chromatographed in petroleumether

Sources & evidence

ORD record
ord-084252ccfb6f4ea3acf17345c2dccc79
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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