4-Hydrazinothiazole-5-carboxylic acid methyl ester → 6-{3-[(4-Carbamimidoylphenylamino)-(2-fluoro-3,5-dimethoxyphenyl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}pyridine-2-carboxylic acid trifluoroacetate

HRID 1161573Notes

Reaction equation

HRID 1161573 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(C1C=CC(NC(C2C=C(OC)C3OCCCOC=3C=2)C2N[C:22](=[O:24])N(C3N=CSC=3C(O)=O)N=2)=CC=1)(=N)N.CO[C:48](=[O:78])[N:49]=[C:50](SC)[C:51]([C:65]1[CH:70]=[C:69]([O:71][CH3:72])[C:68](OC)=[CH:67][C:66]=1[F:75])=[N:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2[N:63]=C(C)O[N:60]=2)=[CH:55][CH:54]=1.Cl.C[O:81][C:82]([C:84]1[CH:89]=[CH:88][CH:87]=[C:86]([NH:90][NH2:91])[N:85]=1)=[O:83].COC(=O)N=C(SC)C(C1C=C(OC)C2OCCCOC=2C=1)=NC1C=CC(C2N=C(C)ON=2)=CC=1.COC(C1SC=NC=1NN)=O>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:59]([C:56]1[CH:57]=[CH:58][C:53]([NH:52][CH:51]([C:65]2[CH:70]=[C:69]([O:71][CH3:72])[CH:68]=[C:67]([O:24][CH3:22])[C:66]=2[F:75])[C:50]2[NH:49][C:48](=[O:78])[N:90]([C:86]3[N:85]=[C:84]([C:82]([OH:81])=[O:83])[CH:89]=[CH:88][CH:87]=3)[N:91]=2)=[CH:54][CH:55]=1)(=[NH:60])[NH2:63]

Participants

6

Reactant 5

HCID 552812984-Hydrazinothiazole-5-carboxylic acid methyl esterHCID 670973026-Hydrazinopyridine-2-carboxylic acid methyl ester hydrochlorideHCID 72312720[2-(9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl esterHCID 72312823[2-(2-Fluoro-4,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl esterHCID 1363892874-{3-[(4-carbamimidoylphenylamino)-(9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiazole-5-carboxylic acid trifluoroacetate

Product 1

HCID 1363892866-{3-[(4-Carbamimidoylphenylamino)-(2-fluoro-3,5-dimethoxyphenyl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}pyridine-2-carboxylic acid trifluoroacetate

Procedure

The same procedure was carried out as in Examples (180a) to (180b), except that [2-(2-fluoro-4,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester and 6-hydrazinopyridine-2-carboxylic acid methyl ester hydrochloride (Example (174a)) were used instead of respectively {2-(9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester and 4-hydrazinothiazole-5-carboxylic acid methyl ester in Example (180a), to give the title compound as a yellow solid.

Sources & evidence

ORD record
ord-3f8714f4d70c483fb5d257da8d4ebd70
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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