2-[(4-(Methanesulfonamido)phenoxy)methyl]oxirane → N-[4-[2-Hydroxy-3-[methyl[(6-nitro-2-quinolinyl)methyl]amino]propoxy]phenyl]methanesulfonamide

HRID 1091089Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of 2-[(4-(methanesulfonamido)phenoxy)methyl]oxirane (5.32 g, 21.89 mmol) in ethanol (140 mL) was added the 2-(methylaminomethyl)-6-nitroquinoline (4.75, 21.89 mmol) and the resulting mixture was stirred at 50° C. overnight. The reaction mixture was cooled, concentrated, and subjected to purification by HPLC (10% methanol-ethyl acetate) to afford 1.96 g of product as a yellow amorphous solid.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated
customsubjected to purification by HPLC (10% methanol-ethyl acetate)

Sources & evidence

ORD record: ord-321889fc4e194ccab578248c3de9135e
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05084463

Reaction notes

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