4-[[2-(4-Tolyl)benzoyl)amino]benzoic acid → (3aR)-5-[4-[[2-(4-Tolyl) Benzoyl]Amino]Benzoyl]-1,2,3,3a,4,5-Hexahydro-Pyrrolo[1,2-a]Quinoxaline

HRID 1976246Notes

Reaction equation

HRID 1976246 reaction equation
[CH2:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][C@H:4]2[CH2:3][CH2:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[C:14]1([CH3:38])[CH:19]=[CH:18][C:17]([C:20]2[CH:37]=[CH:36][CH:35]=[CH:34][C:21]=2[C:22]([NH:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=2)=[O:23])=[CH:16][CH:15]=1>>[C:14]1([CH3:38])[CH:15]=[CH:16][C:17]([C:20]2[CH:37]=[CH:36][CH:35]=[CH:34][C:21]=2[C:22]([NH:24][C:25]2[CH:33]=[CH:32][C:28]([C:29]([N:12]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]4[CH2:1][CH2:2][CH2:3][C@@H:4]4[CH2:13]3)=[O:30])=[CH:27][CH:26]=2)=[O:23])=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 155453824-[[2-(4-Tolyl)benzoyl)amino]benzoic acidHCID 40639603(R)-1,2,3,3A,4,5-hexahydropyrrolo[1,2-a]quinoxaline

Product 1

HCID 20651246(3aR)-5-[4-[[2-(4-Tolyl) Benzoyl]Amino]Benzoyl]-1,2,3,3a,4,5-Hexahydro-Pyrrolo[1,2-a]QuinoxalineYield 31.7%

Procedure

The same procedures used in Example 1 were repeated using (3aR)-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxaline prepared in Reference Example 15 and 4-[[2-(4-tolyl)benzoyl)amino]benzoic acid to give the title compound after recrystallization from ethyl acetate-hexane. Yield 31.7%.

Sources & evidence

ORD record
ord-0d24624d497648cb84c93371dde97147
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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