Morpholine → 6-Bromo-1-[(4-methylphenyl)sulfonyl]-4-[5-(4-morpholinylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazole

HRID 520505Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred mixture of 6-bromo-4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-[(4-methylphenyl)sulfonyl]-1H-indazole (0.1 g, 0.214 mmol) and morpholine (0.056 ml, 0.641 mmol) in acetonitrile (2.5 ml) was heated at 80° C. in the microwave (biotage initiator) for 45 mins. The mixture was evaporated and the residual solid triturated with ether (10 ml) to afford the title compound as a cream coloured solid which was collected by filtration (0.07 g).

Workup

customThe mixture was evaporated
customthe residual solid triturated with ether (10 ml)

Sources & evidence

ORD record: ord-e958335bdee94a55a2991a9a31b4ff54
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326987B2

Reaction notes

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