Morpholine → N-(2,4-dimethylphenyl)-3,5-difluoro-4-(1-hydroxy-2-morpholinoethyl)-N-isobutylbenzenesulfonamide

HRID 1487064Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide (150 mg, 0.379 mmol) in ethanol (1.5 mL) at 25° C. was added morpholine (0.033 ml, 0.379 mmol) and the reaction mixture stirred at 50° C. for 6 hours. The mixture was concentrated in vacuo and purified by mass directed autoprep (ammonium carbonate modifier). The appropriate fractions were combined and evaporated in vacuo to give the required product, 9 mg, as a colourless oil. LCMS [LCMS2] Rt 1.33 min, m/z (ES+) 483 (M+H).

Workup

concentrationThe mixture was concentrated in vacuo
custompurified by mass
customevaporated in vacuo

Sources & evidence

ORD record: ord-544f7cbf5c31420ab6970fbcf80181b5
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428452B2

Reaction notes

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