Morpholine → HCID 67215102, compound

HRID 1983201Notes

Reaction equation

HRID 1983201 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-aa8c9d8ecbae4358972eb3cf12f66614
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

Loading…