Trifluoroacetic acid → 4-{[[1-(3-Aminopyridin-2-yl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-(5-fluoro-8-methoxychroman-6-yl)methyl]amino}benzamidine trifluoroacetate

HRID 1161572Notes

Reaction equation

HRID 1161572 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[C:7]([N:12]2[C:16](=[O:17])[NH:15][C:14]([CH:18]([NH:32][C:33]3[CH:41]=[CH:40][C:36]([C:37]([NH2:39])=[NH:38])=[CH:35][CH:34]=3)[C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21](OCCO)[C:20]=3[F:31])=[N:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1.COC(=O)N=C(SC)C(C1C(F)=C2C(=C(OC)C=1)[O:67][CH2:66][CH2:65][CH2:64]2)=NC1C=CC(C2N=C(C)ON=2)=CC=1.[F:77][C:78]([F:83])([F:82])[C:79]([OH:81])=[O:80].COC(=O)N=C(SC)C(C1C=C(OC)C=C(OCCO[Si](C(C)(C)C)(C)C)C=1F)=NC1C=CC(C2N=C(C)ON=2)=CC=1>C(O)(=O)C>[F:77][C:78]([F:83])([F:82])[C:79]([OH:81])=[O:80].[NH2:5][C:6]1[C:7]([N:12]2[C:16](=[O:17])[NH:15][C:14]([CH:18]([NH:32][C:33]3[CH:41]=[CH:40][C:36]([C:37]([NH2:39])=[NH:38])=[CH:35][CH:34]=3)[C:19]3[C:20]([F:31])=[C:21]4[C:22](=[C:23]([O:25][CH3:26])[CH:24]=3)[O:67][CH2:66][CH2:65][CH2:64]4)=[N:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 72312734[2-(5-Fluoro-8-methoxychroman-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl esterHCID 72312769(2-{3-[2-(t-Butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene)carbamic acid methyl esterHCID 1363892814-({[1-(3-Aminopyridin-2-yl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)benzamidine acetate

Product 1

HCID 1363892854-{[[1-(3-Aminopyridin-2-yl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-(5-fluoro-8-methoxychroman-6-yl)methyl]amino}benzamidine trifluoroacetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The same procedure was carried out as in Examples (200b) to (200c), except that [2-(5-fluoro-8-methoxychroman-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester (Example (33d)) and 0.1% trifluoroacetic acid were used instead of respectively the (2-{3-[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 in Example (200b) and 0.1% acetic acid in Example (200c), to give the title compound.

Sources & evidence

ORD record
ord-fb0a77442c504e8b952ed5b19d7de65d
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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