Morpholine → HCID 57968856, compound

HRID 1471540Notes

Reaction equation

HRID 1471540 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CN(C)C=O.[OH-].[Na+]>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:10]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 221427782,6-Dichloropyridine-3-carboxamide2×

Product 1

HCID 57968856HCID 57968856, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

Refer to synthesis of (D46) for preparation of 2,6-dichloro-nicotinamide (1). A sealed reaction vessel containing 2,6-dichloro-nicotinamide (1) (1.85 g, 9.70 mmol) and morpholine (1.69 mL, 19.4 mmol) in anhydrous dimethylformamide (20 mL) was heated to 50° C. for 2.5 h. The reaction was then cooled to room temperature and diluted with 0.1 M NaOH (600 mL) and extracted with ethyl acetate (3×500 mL). All organics were combined, dried over Na2SO4, filtered and concentrated to give the title compound (2.49 g) as an orange oil, which later solidified upon standing. Compound 6-Chloro-2-morpholin-4-yl-nicotinamide (2) was carried forward without further purification. 1H NMR 400 MHz (d6-DMSO) δ 7.89 (br s, 1H), 7.67 (d, J=7.8 Hz, 1H), 7.56 (br s, 1H), 6.88 (d, J=7.8 Hz, 1H), 3.67 (br t, J=4.7 Hz, 4H), 3.31 (br t, J=4.7 Hz, 4H).

Workup

  1. customRefer to synthesis of (D46)
  2. customA sealed reaction vessel
  3. temperatureThe reaction was then cooled to room temperature
  4. extractionextracted with ethyl acetate (3×500 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bbd6c0b4a6ad4de7b40ddb98418faeaf
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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