Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1) → 5-(3-{(6-Fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-[4-(5-methyl[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1161558Notes

Reaction equation

[F:1]C1C=C(OC)C(OC)=CC=1C(NC1C=CC(C2N=C(C)ON=2)=CC=1)C1NC(=O)N(C2C=CC=CC=2C(O)=O)N=1.CO[C:43](=[O:75])[N:44]=[C:45](SC)[C:46]([C:60]1[CH:70]=[C:69]([O:71][CH3:72])[C:63]2[O:64][CH2:65][CH2:66][CH2:67][O:68][C:62]=2[CH:61]=1)=[N:47][C:48]1[CH:53]=[CH:52][C:51]([C:54]2[N:58]=[C:57]([CH3:59])[O:56][N:55]=2)=[CH:50][CH:49]=1.Cl.Cl.[CH2:78]([O:80][C:81]([C:83]1[C:84]([NH:88][NH2:89])=[N:85][NH:86][CH:87]=1)=[O:82])[CH3:79].COC(=O)N=C(SC)C(C1C=C(OC)C(OC)=CC=1F)=NC1C=CC(C2N=C(C)ON=2)=CC=1.Cl.N(C1C=CC=CC=1C(O)=O)N>>[CH2:78]([O:80][C:81]([C:83]1[CH:87]=[N:86][NH:85][C:84]=1[N:88]1[C:43](=[O:75])[NH:44][C:45]([CH:46]([C:60]2[CH:70]=[C:69]([O:71][CH3:72])[C:63]3[O:64][CH2:65][CH2:66][CH2:67][O:68][C:62]=3[C:61]=2[F:1])[NH:47][C:48]2[CH:49]=[CH:50][C:51]([C:54]3[N:58]=[C:57]([CH3:59])[O:56][N:55]=3)=[CH:52][CH:53]=2)=[N:89]1)=[O:82])[CH3:79]

Participants

Reactant 5

HCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)

HCID 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 ester

HCID 72312823[2-(2-Fluoro-4,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester

HCID 1361246962-(3-{(2-Fluoro-4,5-dimethoxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)benzoic acid

HCID 178469938HCID 178469938, compound

Product 1

HCID 1359820505-(3-{(6-Fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-[4-(5-methyl[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

Procedure

The same procedure was carried out as in Examples (1e) to (1f), except that {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 (Example (30c)) and 3-hydrazino-1H-pyrazole-4-carboxylic acid ethyl ester bishydrochloride (Example (157b)) were used instead of respectively the [2-(2-fluoro-4,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester and 2-hydrazinobenzoic acid hydrochloride in Example (1e), to give the title compound.

Sources & evidence

ORD record: ord-c7d4dc3853cd4a2794579abb6b6745ef
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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