4-Aminobenzonitrile → (S)-3-{3-[(4-Carbamimidoyl-3-fluorophenylamino)-(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

HRID 1161599Notes

Reaction equation

HRID 1161599 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:33][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].[F:39]C1C=C(N)C=CC=1C#N.NC1C=CC(C#N)=CC=1>>[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][O:33][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][C:9]=1[F:39])(=[NH:2])[NH2:3]

Participants

4

Reactant 3

HCID 133964-AminobenzonitrileHCID 27834134-Amino-2-fluorobenzonitrileHCID 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 136389303(S)-3-{3-[(4-Carbamimidoyl-3-fluorophenylamino)-(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

Procedure

The same procedure was carried out as in Examples (168a) to (168d), except that 2-fluoro-4-aminobenzonitrile [CAS No. 53312-80-4] was used instead of 4-aminobenzonitrile in Example (168a), to give the first eluting enantiomer of the title compound.

Sources & evidence

ORD record
ord-e9663efd4bb04a388aa594b2018d77ef
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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