(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one → (3R)-4-(2,4-dihydroxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one

HRID 898248Notes

Reaction equation

HRID 898248 reaction equation
C[O:2][C:3]1[CH:26]=[C:25]([O:27]C)[CH:24]=[CH:23][C:4]=1[C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[N:10]([CH2:18][CH3:19])[C:9](=[O:20])[C@H:8]1[CH2:21][CH3:22])=[O:6].C([C@H]1N(C(=O)C2C=CC(O)=CC=2)C2C(=CC(F)=CC=2)N(C)C1=O)C>>[OH:2][C:3]1[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][C:4]=1[C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[N:10]([CH2:18][CH3:19])[C:9](=[O:20])[C@H:8]1[CH2:21][CH3:22])=[O:6]

Participants

3

Reactant 2

HCID 11709655(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 69220797(3R)-4-(2,4-dimethoxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 11552198(3R)-4-(2,4-dihydroxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-oneYield 31%

Procedure

(3R)-4-(2,4-dimethoxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one was treated according to the procedure for the preparation of (3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one (see Example 1) to yield (3R)-4-(2,4-dihydroxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one (31%). MS (ESI) m/z 359 ([M+H]+); MS (ESI) m/z 357 ([M−H]−); HRMS: calcd for C19H19FN2O4, 358.1329; found (ESI_FT), 359.13972.

Sources & evidence

ORD record
ord-473f49e260c9431eb5bd568f58944eed
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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