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

HRID 898262Notes

Reaction equation

HRID 898262 reaction equation
[C:1](=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)[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:46]=[CH:47][C:48]([OH:51])=[CH:49][CH:50]=2)(=[O:43])=[O:44])[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([CH3:1])[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 11667647(3S)-3-ethyl-4-[(4-hydroxyphenyl)sulfonyl]-1,6-dimethyl-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-4-[(4-hydroxyphenyl)sulfonyl]-1,6-dimethyl-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=−123° (c=0.0057 G/ML, DMSO); MS (ESI) m/z 361 ([M+H]+); MS (ESI) m/z 359 ([M−H]−); Anal. Calcd for C18H20N2O4S: C, 59.98; H, 5.59; N, 7.77. Found: C, 57.75; H, 5.20; N, 7.42.

Sources & evidence

ORD record
ord-4f681e4426a646a48493f9ca90ac4eb4
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

Loading…