Morpholine → HCID 67215083, compound

HRID 1983195Notes

Reaction equation

HRID 1983195 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-38c668d628f44258aa44981dd370d2ed
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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