Morpholine → HCID 67215083, compound

HRID 2421212Notes

Reaction equation

HRID 2421212 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][O:16][C:17]=3[CH3:18])=[N:11][N:12]=2)=[CH:4][N:3]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CS(C)=O.C(OCC)(=O)C>[CH3:18][C:17]1[O:16][N:15]=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]=1[C:10]1[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[N:3][CH:4]=2)=[N:12][N:11]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86613584HCID 86613584, compound

Product 1

HCID 67215083HCID 67215083, compoundYield 70,511.297%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 2-chloro-5-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridine (200 mg, 0.59 mmol) in DMSO (2 mL) was added morpholine (257 mg, 2.95 mmol) and the reaction mixture was heated for 1 h at 160° C. After cooling to ambient temperature it was diluted with ethyl acetate (20 mL) and washed with aqueous sodium carbonate (saturated) and water. Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 70:30) afforded the title compound (162 g, 70%) as a white solid. MS: m/e=390.3 [M+H]+.

Workup

  1. temperatureAfter cooling to ambient temperature it
  2. washwashed with aqueous sodium carbonate (saturated) and water
  3. dry with materialDrying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 70:30)

Sources & evidence

ORD record
ord-e35d5838bf9a47168cdfd7371a6b13c8
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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