Iodoethane → (3S)-1,3-diethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one

HRID 898260Notes

Reaction equation

HRID 898260 reaction equation
C(=O)([O-])OC1C=CC(S(N2C3C(=CC=C(F)C=3)NC(=O)[C@@H]2CC)(=O)=O)=CC=1.ICC.[CH2:31]([C@@H:33]1[N:42]([S:43]([C:46]2[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=2)(=[O:45])=[O:44])[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([F:53])[CH:40]=2)[N:35]([CH2:54][CH2:55]C)[C:34]1=[O:57])[CH3:32]>>[CH2:54]([N:35]1[C:36]2[C:41](=[CH:40][C:39]([F:53])=[CH:38][CH:37]=2)[N:42]([S:43]([C:46]2[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=2)(=[O:45])=[O:44])[C@@H:33]([CH2:31][CH3:32])[C:34]1=[O:57])[CH3:55]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 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 11610549(3S)-1,3-diethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-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 iodoethane 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)-1,3-diethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=−7° (c=0.0077 G/ML, DMSO); MS (ESI) m/z 379 ([M+H]+); MS (ESI) m/z 377 ([M−H]−); HRMS: calcd for C18H19FN2O4S, 378.1050; found (ESI+), 379.11178.

Sources & evidence

ORD record
ord-eff99a2869944c65ae0f5158d4e4f279
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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