2-Hydrazinylpyrimidine → (S)-4-({(3,5-Dimethoxyphenyl)-[1-(3-methylpyridin-2-yl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]methyl}amino)benzamidine acetate

HRID 1161595Notes

Reaction equation

HRID 1161595 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].CO[C:7]1[CH:8]=[C:9]([C@H:16](NC2C=CC(C(N)=N)=CC=2)[C:17]2[NH:21][C:20](=O)[N:19](C3N=CC=CN=3)[N:18]=2)C=C(COC)C=1.C[O:40][C:41](=O)[N:42]=[C:43](SC)[C:44]([C:58]1[CH:63]=[C:62]([O:64][CH3:65])[CH:61]=[C:60]([O:66][CH3:67])[CH:59]=1)=[N:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2[N:56]=C(C)O[N:53]=2)=[CH:48][CH:47]=1.CC1N=C(NN)C=CC=1.COC(=O)N=C(SC)C(C1C=C(COC)C=C(OC)C=1)=NC1C=CC(C2N=C(C)ON=2)=CC=1.N(C1N=CC=CN=1)N>>[C:1]([OH:4])(=[O:3])[CH3:2].[CH3:65][O:64][C:62]1[CH:63]=[C:58]([C@H:44]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]([NH2:56])=[NH:53])=[CH:48][CH:47]=2)[C:43]2[NH:42][C:41](=[O:40])[N:19]([C:20]3[C:8]([CH3:7])=[CH:9][CH:16]=[CH:17][N:21]=3)[N:18]=2)[CH:59]=[C:60]([O:66][CH3:67])[CH:61]=1

Participants

6

Reactant 5

HCID 3465582-HydrazinylpyrimidineHCID 135904652-Hydrazinyl-6-methylpyridineHCID 72312743{2-(3-Methoxy-5-methoxymethylphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterHCID 72312837{2-(3,5-Dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterHCID 136366210(S)-4-{[(3-methoxy-5-methoxymethylphenyl)-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate

Product 1

HCID 136389298(S)-4-({(3,5-Dimethoxyphenyl)-[1-(3-methylpyridin-2-yl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]methyl}amino)benzamidine acetate

Procedure

The same procedure was carried out as in Examples (10d) to (10e), except that {2-(3,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester and (6-methylpyridin-2-yl)hydrazine [CAS No. 5315-24-2] were used instead of respectively {2-(3-methoxy-5-methoxymethylphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester and 2-hydrazinopyrimidine in Example (10d), to give the first eluting enantiomer of the title compound.

Sources & evidence

ORD record
ord-c05594a16b9044b3944cae2f0c338d5b
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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