Methyl iodide → HCID 11495564, compound

HRID 898273Notes

Reaction equation

HRID 898273 reaction equation
C(=O)(OCC)[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([Br:22])=[CH:19][CH:20]=3)[NH:15][C:14](=[O:23])[C@@H:13]2[CH2:24][CH3:25])(=[O:11])=[O:10])=[CH:5][CH:4]=1.IC.[CH2:32]([C@@H]1N(S(C2C=CC(O)=CC=2)(=O)=O)C2C(=CC=C(F)C=2)N(CCC)C1=O)C>>[Br:22][C:18]1[CH:17]=[C:16]2[C:21]([N:12]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[C@@H:13]([CH2:24][CH3:25])[C:14](=[O:23])[N:15]2[CH3:32])=[CH:20][CH:19]=1

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 69222753HCID 69222753, compound

Product 1

HCID 11495564HCID 11495564, compound

Procedure

4-{[(2S)-6-Bromo-2-ethyl-3-oxo-3,4-dihydroquinoxalin-1 (2H)-yl]sulfonyl}phenyl ethyl carbonate 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)-7-bromo-3-ethyl-4-[(4-hydroxyphenyl)sulfonyl]-1-methyl-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=−121° (c=0.0052 G/ML, DMSO); MS (ESI) m/z 425/427 ([M+H]+); MS (ESI) m/z 423/425 ([M−H]−); Anal. Calcd for C17H17BrN2O4S: C, 48.01; H, 4.03; N, 6.59. Found: C, 47.74; H, 4.17; N, 6.22.

Sources & evidence

ORD record
ord-d85da79a1b094d91bcf0a82cb6af9514
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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