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

HRID 898261Notes

Reaction equation

HRID 898261 reaction equation
C(=O)([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=3)[NH:18][C:17](=[O:26])[C@@H:16]2[CH2:27][CH3:28])(=[O:14])=[O:13])=[CH:8][CH:7]=1)OCC.I[CH2:31][CH3:32].C([C@@H]1N(S(C2C=CC(O)=CC=2)(=O)=O)C2C(=CC=C(F)C=2)N(CCC)C1=O)C>CS(C)=O>[CH2:31]([N:18]1[C:19]2[C:24](=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[N:15]([S:12]([C:9]2[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=2)(=[O:13])=[O:14])[C@@H:16]([CH2:27][CH3:28])[C:17]1=[O:26])[CH3:32]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11538398(3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 69223608Ethyl 4-{[(2S)-2-ethyl-7-methyl-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate

Product 1

HCID 11660774(3S)-1,3-diethyl-4-[(4-hydroxyphenyl)sulfonyl]-6-methyl-3,4-dihydroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 4-{[(2S)-2-ethyl-7-methyl-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate 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-4-[(4-hydroxyphenyl)sulfonyl]-6-methyl-3,4-dihydroquinoxalin-2(1H)-one [α]D25=−118° (c=0.0054 G/ML, DMSO); MS (ESI) m/z 375 ([M+H]+); MS (ESI) m/z 373 ([M−H]−); Anal. Calcd for C19H22N2O4S: C, 60.94; H, 5.92; N, 7.48. Found: C, 61.50; H, 5.99; N, 6.89.

Sources & evidence

ORD record
ord-b321e9a2e70446ff9eb25ef68807a78a
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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