Methyl 3-Hydrazinothiophene-2-Carboxylate → (S)-3-(3-{(4-Carbamimidoylphenylamino)-[3-(2-hydroxyethoxy)-4,5-dimethoxyphenyl]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)thiophene-2-carboxylic acid

HRID 1161598Notes

Reaction equation

HRID 1161598 reaction equation
CO[C:3](=[O:33])[N:4]=[C:5](SC)[C:6]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([OH:30])[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.C[O:35][C:36]([C:38]1[S:39][CH:40]=[CH:41][C:42]=1[NH:43][NH2:44])=[O:37].COC(=O)N=C(SC)C(C1C=C(OC)C=C(O)C=1F)=NC1C=CC(C2N=[C:61]([CH3:63])[O:60]N=2)=CC=1.COC(C1SC=NC=1NN)=O>>[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][CH3:29])=[C:22]([O:30][CH2:63][CH2:61][OH:60])[CH:21]=2)[C:5]2[NH:4][C:3](=[O:33])[N:43]([C:42]3[CH:41]=[CH:40][S:39][C:38]=3[C:36]([OH:35])=[O:37])[N:44]=2)=[CH:13][CH:12]=1)(=[NH:18])[NH2:15]

Participants

5

Reactant 4

HCID 2777595Methyl 3-Hydrazinothiophene-2-CarboxylateHCID 552812984-Hydrazinothiazole-5-carboxylic acid methyl esterHCID 72312728{2-(3-Hydroxy-4,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterHCID 72312745[2-(2-Fluoro-3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester

Product 1

HCID 136389302(S)-3-(3-{(4-Carbamimidoylphenylamino)-[3-(2-hydroxyethoxy)-4,5-dimethoxyphenyl]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)thiophene-2-carboxylic acid

Procedure

The same procedure was carried out as in Example 167, except that {2-(3-hydroxy-4,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (159a)) and 3-hydrazinothiophene-2-carboxylic acid methyl ester were used instead of respectively the [2-(2-fluoro-3-hydroxy-5-methoxyphenyl)-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, to give the first eluting enantiomer of the title compound.

Sources & evidence

ORD record
ord-c0b38380ad444a8ebd566bdddedbe771
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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