Morpholine → HCID 67215102, compound

HRID 2421218Notes

Reaction equation

HRID 2421218 reaction equation
Br[C:2]1[CH:3]=[CH:4][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)=[N:6][CH:7]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.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[N:6]=[CH:7][C:2]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:3][CH:4]=2)=[N:12][N:11]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 67215572HCID 67215572, compound

Product 1

HCID 67215102HCID 67215102, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-2-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridine (200 mg, 0.52 mmol), morpholine (455 μL, 5.22 mmol) and tetrabutylammonium iodide (41 mg, 0.10 mmol) was irradiated in the microwave for 1.5 h at 160° C. After cooling to ambient temperature the resulting suspension was diluted with ethyl acetate (15 mL) and stirred for 15 min at this temperature. Filtering off and washing with water (2 mL) and with ethyl acetate (1 mL) afforded the title compound (95 mg, 47%) which was obtained as a light brown solid. MS: m/e=390.3 [M+H]+.

Workup

  1. customwas irradiated in the microwave for 1.5 h at 160° C
  2. filtrationFiltering off
  3. washwashing with water (2 mL) and with ethyl acetate (1 mL)

Sources & evidence

ORD record
ord-2d31404801fd4299a126339bb1a715e0
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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