Morpholine → N-(5-chloro-2-fluorophenyl)-4-(1-hydroxy-2-morpholinoethyl)-N-isobutylbenzenesulfonamide

HRID 1487066Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of N-(5-chloro-2-fluorophenyl)-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide (200 mg, 0.521 mmol) in ethanol (2 mL) at 25° C. was added morpholine (0.045 ml, 0.521 mmol) and the reaction mixture stirred at 50° C. for 24 hours. The mixture was then purified by mass directed autoprep (ammonium carbonate modifier). The appropriate fractions were combined and evaporated in vacuo to give the required product, 51.4 mg. LCMS [LCMS2] Rt 1.25 min, m/z (ES+) 471 (M+H).

Workup

customThe mixture was then purified by mass
customevaporated in vacuo

Sources & evidence

ORD record: ord-e504f2459d394d45b64471836712f15a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428452B2

Reaction notes

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