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

HRID 1976240Notes

Reaction equation

HRID 1976240 reaction equation
[OH:1][C@H:2]1[CH2:14][N:5]2[C:6]3[C:11]([NH:12][CH2:13][C@@H:4]2[CH2:3]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[C:15]1([CH3:39])[CH:20]=[CH:19][C:18]([C:21]2[CH:38]=[CH:37][CH:36]=[CH:35][C:22]=2[C:23]([NH:25][C:26]2[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=2)=[O:24])=[CH:17][CH:16]=1>>[OH:1][C@H:2]1[CH2:14][N:5]2[C:6]3[C:11]([N:12]([C:30](=[O:31])[C:29]4[CH:28]=[CH:27][C:26]([NH:25][C:23](=[O:24])[C:22]5[CH:35]=[CH:36][CH:37]=[CH:38][C:21]=5[C:18]5[CH:17]=[CH:16][C:15]([CH3:39])=[CH:20][CH:19]=5)=[CH:34][CH:33]=4)[CH2:13][C@@H:4]2[CH2:3]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

3

Reactant 2

HCID 155453824-[[2-(4-Tolyl)benzoyl)amino]benzoic acidHCID 15545386(2R,3aS)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoxalin-2-ol

Product 1

HCID 12042759(2R,3aS)-2-Hydroxy-5-[4-[[2-(4-Tolyl)Benzoyl] Amino]Benzoyl]-1,2,3,3a,4,5-Hexahydro-Pyrrolo[1,2-a]QuinoxalineYield 55%

Procedure

The same procedures used in Example 1 were repeated using (2R, 3aS)-2-hydroxy-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxaline prepared in Reference Example 16 and 4-[[2-(4-tolyl)benzoyl]amino]benzoic acid to give the title compound after recrystallization from ethyl acetate-hexane. m.p.: 163-164.5° C.; Yield 55.0%.

Sources & evidence

ORD record
ord-0d13d1865ddc4ef9877640f83064e779
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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