(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one → HCID 11567129, compound

HRID 898246Notes

Reaction equation

HRID 898246 reaction equation
[CH:1]1([N:6]2[C:15]3[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=3)[N:9]([C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=3)[C@H:8]([CH2:27][CH3:28])[C:7]2=[O:29])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([C@H]1N(C(=O)C2C=CC(O)=CC=2)C2C(=CC(F)=CC=2)N(C)C1=O)C>>[CH:1]1([N:6]2[C:15]3[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=3)[N:9]([C:17](=[O:26])[C:18]3[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)[C@H:8]([CH2:27][CH3:28])[C:7]2=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 11709655(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 69222020HCID 69222020, compound

Product 1

HCID 11567129HCID 11567129, compoundYield 40%

Procedure

(3R)-1-Cyclopentyl-3-ethyl-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-cyclopentyl-3-ethyl-6-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (40%). [α]D25=−309° (c=0.0095 G/ML, CHCl3); MS (ESI) m/z 383 ([M+H]+); MS (ESI) m/z 381 ([M−H]−); HRMS: calcd for C22H23FN2O3, 382.1693; found (ESI_FT), 383.17555.

Sources & evidence

ORD record
ord-d83acd19058f4dee923422221461fbd4
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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