3-Fluoro-2-hydrazinylpyridine → 2-Hydrazinyl-3-nitropyridine

HRID 1161470Notes

Reaction equation

HRID 1161470 reaction equation
C[O:2][C:3](=[O:32])[N:4]=[C:5](SC)[C:6]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([O:28][CH3:29])[CH:21]=1)=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=C(C)[O:16][N:15]=2)=[CH:10][CH:9]=1.[F:33][C:34]1[C:35]([NH:40][NH2:41])=[N:36][CH:37]=[CH:38][CH:39]=1.C[O:43]C(=O)N=C(SC)C(C1C=C(C)N=[C:63]([O:68]C)[CH:62]=1)=NC1C=CC(C2N=C(C)ON=2)=CC=1>>[N+:15]([C:34]1[C:35]([NH:40][NH2:41])=[N:36][CH:37]=[CH:38][CH:39]=1)([O-:16])=[O:43].[C:63]([OH:68])(=[O:2])[CH3:62].[CH3:29][O:28][C:22]1[CH:21]=[C:20]([CH:6]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH2:15])=[NH:18])=[CH:12][CH:13]=2)[C:5]2[NH:4][C:3](=[O:32])[N:40]([C:35]3[C:34]([F:33])=[CH:39][CH:38]=[CH:37][N:36]=3)[N:41]=2)[CH:25]=[C:24]([O:26][CH3:27])[N:23]=1

Participants

5

Reactant 3

HCID 269852863-Fluoro-2-hydrazinylpyridineHCID 72312723{2-(2,6-Dimethoxypyridin-4-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterHCID 72312832{2-(2-Methoxy-6-methylpyridin-4-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

Product 2

HCID 35789352-Hydrazinyl-3-nitropyridineHCID 1363661684-{[(2,6-dimethoxypyridin-4-yl)-[1-(3-fluoropyridin-2-yl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate

Procedure

The same procedure was carried out as in Example (19c), except that {2-(2,6-dimethoxypyridin-4-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester and (3-fluoropyridin-2-yl)hydrazine were used instead of respectively the {2-(2-methoxy-6-methylpyridin-4-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester and the (3-nitropyridin-2-yl)hydrazine, to give 4-{[(2,6-dimethoxypyridin-4-yl)-[1-(3-fluoropyridin-2-yl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate.

Sources & evidence

ORD record
ord-9985cca7fb1a475eb869f9c177ba3879
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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