2,6-Dimethylmorpholine → HCID 89852598, compound

HRID 1746901Notes

Reaction equation

HRID 1746901 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[N:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=1.[CH3:19][CH:20]1[O:25][CH:24]([CH3:26])[CH2:23][NH:22][CH2:21]1>C(#N)C>[CH3:26][CH:24]1[CH2:23][N:22]([CH2:2][C:3]2[CH:7]=[CH:6][N:5]([C:8]3[N:18]=[CH:17][CH:16]=[CH:15][C:9]=3[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=2)[CH2:21][CH:20]([CH3:19])[O:25]1

Participants

4

Reactant 2

HCID 1108622,6-DimethylmorpholineHCID 89851983HCID 89851983, compound

Product 1

HCID 89852598HCID 89852598, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-(3-(chloromethyl)-1H-pyrazol-1-yl)nicotinate (650 mg, 2.446 mmol), 2,6-dimethylmorpholine (0.482 mL, 3.91 mmol) and K2 CO3 (1082 mg, 7.83 mmol) in acetonitrile (25 mL) were stirred over night at room temperature. The mixture was concentrated, the remaining solid partitioned between 60 mL of water and dichloromethane, the organic layer separated, dried (MgSO4), filtered and concentrated again to yield 870 mg of the title compound as clear oil; ESI-MS [M+H]+: 345.2.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe remaining solid partitioned between 60 mL of water and dichloromethane
  3. customthe organic layer separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated again

Sources & evidence

ORD record
ord-b1f81aad12334fffab65960b4a774082
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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