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

HRID 898230Notes

Reaction equation

HRID 898230 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[N:6]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)[C@H:5]([CH2:24][CH3:25])[C:4]1=[O:26])[CH3:2].C([C@H]1N(C(=O)C2C=CC(O)=CC=2)C2C(=CC(F)=CC=2)N(C)C1=O)C>>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[N:6]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C@H:5]([CH2:24][CH3:25])[C:4]1=[O:26])[CH3:2]

Participants

3

Reactant 2

HCID 11709655(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 69221429(3R)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 11501043(3R)-1,3-diethyl-6-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneYield 83%

Procedure

(3R)-1,3-Diethyl-6-fluoro-4-(4-methoxybenzoyl)-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)-1,3-diethyl-6-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (83%). [α]D25=−300° (c=0.010 G/ML, CHCl3); MS (ESI) m/z 343 ([M+H]+); MS (ESI) m/z 341 ([M−H]−); HRMS: calcd for C19H19FN2O3, 342.1380; found (ESI_FT), 343.14482.

Sources & evidence

ORD record
ord-7359ac46e4464386a712f4c429043b91
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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