[2-(4-Cyanophenylimino)-2-(4-fluoro-7-methoxy-2,3-dihydrobenzofuran-5-yl)-1-methylsulfanylethylidene]carbamic acid methyl ester → (S)-3-{3-[(4-Carbamimidoylphenylamino)-(4-fluoro-7-methoxy-2,3-dihydrobenzofuran-5-yl)methyl]-5-oxo-4,5-dihydro[1,2,4]triazol-1-yl}thiophene-2-carboxylic acid

HRID 1161577Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@@H:11]([C:26]2[CH:35]=[C:34]([O:36][CH3:37])[C:29]3[O:30][CH2:31][CH2:32]O[C:28]=3[C:27]=2[F:38])[C:12]2[NH:16][C:15](=[O:17])[N:14]([C:18]3[CH:22]=[CH:21][S:20][C:19]=3[C:23]([OH:25])=[O:24])[N:13]=2)=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].COC(=O)N=C(SC)C(=NC1C=CC(C#N)=CC=1)C1C=C(OC)C2OCCC=2C=1F>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C@@H:11]([C:26]2[CH:35]=[C:34]([O:36][CH3:37])[C:29]3[O:30][CH2:31][CH2:32][C:28]=3[C:27]=2[F:38])[C:12]2[NH:16][C:15](=[O:17])[N:14]([C:18]3[CH:22]=[CH:21][S:20][C:19]=3[C:23]([OH:25])=[O:24])[N:13]=2)=[CH:8][CH:9]=1)(=[NH:3])[NH2:2]

Participants

Reactant 2

HCID 72312842[2-(4-Cyanophenylimino)-2-(4-fluoro-7-methoxy-2,3-dihydrobenzofuran-5-yl)-1-methylsulfanylethylidene]carbamic acid methyl ester

HCID 136389292(S)-3-{3-[(4-carbamimidoylphenylamino)-(5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}thiophene-2-carboxylic acid

Product 1

HCID 136389291(S)-3-{3-[(4-Carbamimidoylphenylamino)-(4-fluoro-7-methoxy-2,3-dihydrobenzofuran-5-yl)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 Examples (168b) to (168d), except that [2-(4-cyanophenylimino)-2-(4-fluoro-7-methoxy-2,3-dihydrobenzofuran-5-yl)-1-methylsulfanylethylidene]carbamic acid methyl ester (Example (161b)) was used instead of [2-(4-cyanophenylimino)-2-(5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)-1-methylsulfanylethylidene]carbamic acid methyl ester in Example (168b), to give the first eluting enantiomer of the title compound.

Sources & evidence

ORD record: ord-ff1368b8dc3c48158ceab43c6f9ff827
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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