Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1) → (S)-2-(3-{(4-carbamimidoylphenylamino)-[2-fluoro-4-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)benzoic acid

HRID 1161538Notes

Reaction equation

HRID 1161538 reaction equation
CO[C:3](=[O:42])[N:4]=[C:5](SC)[C:6]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH2:29][CH2:30][O:31][Si](C(C)(C)C)(C)C)=[CH:22][C:21]=1[F:39])=[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.Cl.[NH:44]([C:46]1[CH:54]=[CH:53][CH:52]=[CH:51][C:47]=1[C:48]([OH:50])=[O:49])[NH2:45].COC(=O)N=C(SC)C(C1C=C(OC)C=C(OCCF)C=1F)=NC1C=CC(C2N=C(C)ON=2)=CC=1.N(C1N=CC=CN=1)N>>[C:14]([C:11]1[CH:10]=[CH:9][C:8]([NH:7][C@@H:6]([C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH2:29][CH2:30][OH:31])=[CH:22][C:21]=2[F:39])[C:5]2[NH:4][C:3](=[O:42])[N:44]([C:46]3[CH:54]=[CH:53][CH:52]=[CH:51][C:47]=3[C:48]([OH:50])=[O:49])[N:45]=2)=[CH:13][CH:12]=1)(=[NH:18])[NH2:15]

Participants

5

Reactant 4

HCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)HCID 3465582-HydrazinylpyrimidineHCID 72312758{2-[2-Fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterHCID 72312764(2-{4-[2-(t-Butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene)carbamic acid methyl ester

Product 1

HCID 136389276(S)-2-(3-{(4-carbamimidoylphenylamino)-[2-fluoro-4-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)benzoic acid

Procedure

The same procedure was carried out as in Examples (3f)-(3h), except that (2-{4-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene)carbamic acid methyl ester and 2-hydrazinobenzoic acid hydrochloride were used instead of respectively the {2-[2-fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in Example (3f) and 2-hydrazinopyrimidine in Example (3f), to give the title compound as a white solid.

Sources & evidence

ORD record
ord-6eb69b2c07654a0eb02d9c402c4833e5
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

Loading…