m-Anisoyl chloride → (3R)-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 898217Notes

Reaction equation

HRID 898217 reaction equation
[CH2:1]([C@H:3]1[NH:12][C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:14])[CH3:2].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21].C([C@H]1N(C(=O)C2C=CC(OC)=CC=2)C2C(=CC(F)=CC=2)NC1=O)C>>[CH2:1]([C@H:3]1[N:12]([C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[C:17]([O:16][CH3:15])[CH:18]=2)[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:14])[CH3:2]

Participants

4

Reactant 3

HCID 74374m-Anisoyl chlorideHCID 69220784(3R)-3-Ethyl-7-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 69221447(3R)-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneYield 76%

Procedure

(3R)-3-Ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one (see Example 1) was treated with 3-methoxybenzoyl chloride 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 (3R)-3-ethyl-7-fluoro-4-(3-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (76%). MS (ESI) m/z 329 ([M+H]+); MS (ESI) m/z 327 ([M−H]−); HRMS: calcd for C18H17FN2O3, 328.12238; found (ESI+), 329.12924.

Sources & evidence

ORD record
ord-2d49c9fc4b32439a8c5d73687cce53b2
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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