Methyl iodide → (3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898259Notes

Reaction equation

HRID 898259 reaction equation
C(=O)([O-])OC1C=CC(S(N2C3C(=CC=C(F)C=3)NC(=O)[C@@H]2CC)(=O)=O)=CC=1.IC.[CH2:30]([C@@H:32]1[N:41]([S:42]([C:45]2[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=2)(=[O:44])=[O:43])[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([F:52])[CH:39]=2)[N:34]([CH2:53]CC)[C:33]1=[O:56])[CH3:31]>>[CH2:30]([C@@H:32]1[N:41]([S:42]([C:45]2[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=2)(=[O:43])=[O:44])[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([F:52])[CH:39]=2)[N:34]([CH3:53])[C:33]1=[O:56])[CH3:31]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 11538398(3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 866027294-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate

Product 1

HCID 11574128(3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one

Procedure

4-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1 (2H)-yl]sulfonyl}phenyl carbonate (see Example 20) was treated with iodomethane according to the procedure for the preparation of (3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-one (see Example 20) to yield (3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=−14° (c=0.0041 G/ML, DMSO); MS (ESI) m/z 365 ([M+H]+); MS (ESI) m/z 363 ([M−H]−); HRMS: calcd for C17H17FN2O4S, 364.0893; found (ESI+), 365.09603.

Sources & evidence

ORD record
ord-d26735dfd92840438ad44baf35b71898
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

Loading…