4-Methoxybenzenesulfonyl chloride → (3S)-3-ethyl-7-fluoro-4-[(4-methoxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one

HRID 898265Notes

Reaction equation

HRID 898265 reaction equation
[CH2:1]([C@@H:3]1[NH:12][C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:14])[CH3:2].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(=O)(OC1C=CC(S(N2C3C(=CC=C(F)C=3)NC(=O)[C@@H]2CC)(=O)=O)=CC=1)OCC>>[CH2:1]([C@@H:3]1[N:12]([S:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[CH:22][CH:21]=2)(=[O:25])=[O:24])[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:14])[CH3:2]

Participants

4

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 69221470(3S)-3-ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-oneHCID 69224101ethyl 4-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate

Product 1

HCID 69223907(3S)-3-ethyl-7-fluoro-4-[(4-methoxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one

Procedure

(3S)-3-Ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one was treated with 4-methoxybenzenesulfonyl chloride according to the procedure for the preparation of ethyl 4-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1 (2H)-yl]sulfonyl}phenyl carbonate (see Example 20) to yield (3S)-3-ethyl-7-fluoro-4-[(4-methoxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=−12.1° (c=0.006 G/ML, DMSO); MS (ESI) m/z 365 ([M+H]+); MS (ESI) m/z 363 ([M−H]−); Anal. Calcd for C17H17FN2O4S: C, 56.03; H, 4.70; N, 7.69. Found: C, 55.99; H, 4.57; N, 7.62.

Sources & evidence

ORD record
ord-df1abbd989ea434daa84e91ee649a56f
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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