(3S)-3-Ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one → (3S)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 898221Notes

Reaction equation

HRID 898221 reaction equation
[CH2:1]([C@@H:3]1[NH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:13])[CH:10]=2)[NH:5][C:4]1=[O:14])[CH3:2].C([C@H]1N([C:27](=[O:36])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)C2C(=CC(F)=CC=2)NC1=O)C>CCOCC>[CH2:1]([C@@H:3]1[N:12]([C:27](=[O:36])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:13])[CH:10]=2)[NH:5][C:4]1=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 49857655(3S)-3-Ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-oneHCID 69224280(3R)-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 69223582(3S)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(3S)-3-Ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one in ether was treated according to the procedure for the preparation of (3R)-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 1) to yield (3S)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (82%). MS (ESI) m/z 329 ([M+H]+); MS (ESI) m/z 327 ([M−H]−).

Sources & evidence

ORD record
ord-5fec4b9753a74f2289db9cbbb321d2e8
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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