Morpholine → HCID 16722361, compound

HRID 1983182Notes

Reaction equation

F[C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[O:10][C:11]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:16][O:17][C:18]=3[CH3:19])=[N:12][N:13]=2)=[C:4]([O:26][CH3:27])[CH:3]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[F:8][C:7]1[CH:6]=[C:5]([C:9]2[O:10][C:11]([C:14]3[C:15]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[N:16][O:17][C:18]=3[CH3:19])=[N:12][N:13]=2)[C:4]([O:26][CH3:27])=[CH:3][C:2]=1[N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

Reactant 2

HCID 8083Morpholine

HCID 16723008HCID 16723008, compound

Product 1

HCID 16722361HCID 16722361, compoundYield 11%

Procedure

As described for example 26, 2-(4,5-difluoro-2-methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole (153 mg, 0.41 mmol) instead of 2-(4-fluoro-2-methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole was converted using morpholine instead of thiomorpholine to the title compound (SiO2, heptane:ethyl acetate:methanol=60:40:0 to 0:95:5, 20 mg, 11%) which was obtained as an off-white solid. MS: m/e=437.0 [M+H]+.

Sources & evidence

ORD record: ord-86d325a65b9d4fdf90063d0923c0e6c0
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541372B2

Reaction notes

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