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

HRID 898237Notes

Reaction equation

HRID 898237 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[N:8]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)[C@H:7]([CH2:26][CH3:27])[C:6]1=[O:28])[CH2:2][CH2:3][CH3:4].C([C@H]1N(C(=O)C2C=CC(O)=CC=2)C2C(=CC(F)=CC=2)N(C)C1=O)C>>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[N:8]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C@H:7]([CH2:26][CH3:27])[C:6]1=[O:28])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 11709655(3R)-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 69221484(3R)-1-butyl-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 11696372(3R)-1-butyl-3-ethyl-6-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneYield 94%

Procedure

(3R)-1-Butyl-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-butyl-3-ethyl-6-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (94%). [α]D25=−268° (c=0.0103G/ML, CHCl3); MS (ESI) m/z 371 ([M+H]+); MS (ESI) m/z 369 ([M−H]−); HRMS: calcd for C21H23FN2O3, 370.1693; found (ESI_FT), 371.17594; Anal. Calcd for C21H23FN2O3: C, 68.09; H, 6.26; N, 7.56. Found: C, 67.96; H, 6.60; N, 7.67.

Sources & evidence

ORD record
ord-af1f6a01655a4a9f94af50ad927ad6cb
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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