2-Hydrazinylpyrimidine → 2-(4-{(4-carbamimidoyl-phenylamino)-[1-(3-methoxy-pyridin-2-yl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]methyl}-2-ethoxy-phenoxy)-N-methyl-acetamide acetate

HRID 1161484Notes

Reaction equation

HRID 1161484 reaction equation
CO[C:3](=[O:37])[N:4]=[C:5](SC)[C:6]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28](=[O:31])[NH:29][CH3:30])=[C:22]([O:32][CH2:33][CH3:34])[CH:21]=1)=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=C(C)O[N:15]=2)=[CH:10][CH:9]=1.[CH3:38][O:39][C:40]1[C:41]([NH:46][NH2:47])=[N:42][CH:43]=[CH:44][CH:45]=1.COC(=O)N=C(SC)C(C1C=C(OC)C2OCOCC=2C=1)=NC1C=CC(C2N=C(C)ON=2)=CC=1.N(C1N=CC=CN=1)N>>[C:33]([OH:39])(=[O:32])[CH3:34].[C:14]([C:11]1[CH:12]=[CH:13][C:8]([NH:7][CH:6]([C:5]2[NH:4][C:3](=[O:37])[N:46]([C:41]3[C:40]([O:39][CH3:38])=[CH:45][CH:44]=[CH:43][N:42]=3)[N:47]=2)[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([NH:29][CH3:30])=[O:31])=[C:22]([O:32][CH2:33][CH3:34])[CH:21]=2)=[CH:9][CH:10]=1)(=[NH:18])[NH2:15]

Participants

5

Reactant 4

HCID 3465582-HydrazinylpyrimidineHCID 185454042-Hydrazinyl-3-methoxypyridineHCID 72312724[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 esterHCID 72312806{2-(3-Ethoxy-4-methylcarbamoylmethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

Product 1

HCID 1363665982-(4-{(4-carbamimidoyl-phenylamino)-[1-(3-methoxy-pyridin-2-yl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]methyl}-2-ethoxy-phenoxy)-N-methyl-acetamide acetate

Procedure

The same procedure was carried out as in Examples (21i)-(21j), except that {2-(3-ethoxy-4-methylcarbamoylmethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester and (3-methoxy-pyridin-2-yl)hydrazine were used instead of respectively the {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 (21i) and 2-hydrazinopyrimidine in Example (21i), to give the title compound.

Sources & evidence

ORD record
ord-4cf6e27456c0435e9963e255b2e129db
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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