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

HRID 898233Notes

Reaction equation

HRID 898233 reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[N:7]([C:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[C@H:6]([CH2:25][CH3:26])[C:5]1=[O:27])[CH:2]=[CH2:3].C([C@H]1N(C(=O)C2C=CC(O)=CC=2)C2C(=CC(F)=CC=2)N(C)C1=O)C>>[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[N:7]([C:15](=[O:24])[C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[C@H:6]([CH2:25][CH3:26])[C:5]1=[O:27])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 11709655(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 69222655(3R)-1-allyl-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 11566547(3R)-1-allyl-3-ethyl-6-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneYield 97%

Procedure

(3R)-1-Allyl-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 9) 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-allyl-3-ethyl-6-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (97%). [α]D25=−285° (c=0.0102 G/ML, CHCl3); MS (ESI) m/z 355 ([M+H]+); MS (ESI) m/z 353 ([M−H]−); HRMS: calcd for C20H19FN2O3, 354.1380; found (ESI_FT), 355.1449.

Sources & evidence

ORD record
ord-ba94454d49644e318344f3ba907868c2
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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