{2-(3,5-Dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester → (S)-4-{3-[(4-Carbamimidoylphenylamino)-(3,5-dimethoxyphenyl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiazole-5-carboxylic acid

HRID 1161600Notes

Reaction equation

HRID 1161600 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@@H:11]([C:26]2[CH:27]=[C:28]([O:36][CH3:37])[C:29]3OCOC[C:30]=3[CH:35]=2)[C:12]2[NH:16][C:15](=[O:17])[N:14]([C:18]3[N:19]=[CH:20][S:21][C:22]=3[C:23]([OH:25])=[O:24])[N:13]=2)=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[CH3:38][O:39]C(=O)N=C(SC)C(C1C=C(OC)C=C(OC)C=1)=NC1C=CC(C2N=C(C)ON=2)=CC=1>>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@@H:11]([C:26]2[CH:27]=[C:28]([O:36][CH3:37])[CH:29]=[C:30]([O:39][CH3:38])[CH:35]=2)[C:12]2[NH:16][C:15](=[O:17])[N:14]([C:18]3[N:19]=[CH:20][S:21][C:22]=3[C:23]([OH:25])=[O:24])[N:13]=2)=[CH:6][CH:5]=1)(=[NH:3])[NH2:2]

Participants

3

Reactant 2

HCID 72312837{2-(3,5-Dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterHCID 136389305(S)-4-{3-[(4-carbamimidoylphenylamino)-(8-methoxy-4H-benzo[1,3]dioxin-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiazole-5-carboxylic acid

Product 1

HCID 136389304(S)-4-{3-[(4-Carbamimidoylphenylamino)-(3,5-dimethoxyphenyl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiazole-5-carboxylic acid

Procedure

The same procedure was carried out as in Examples (166a) to (166c), except that {2-(3,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (225a)) was used instead of [2-(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester in Example (166a), to give the first eluting enantiomer of the title compound.

Sources & evidence

ORD record
ord-ba7428e46b254e24ab3f4ad0395630d0
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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