5-hydrazino-1H-pyrazole-4-carboxylic acid benzyl ester bishydrochloride → 5-{3-[{3-[3-(t-Butyldimethylsilanyloxy)propoxy]-2-fluoro-5-methoxyphenyl}-(4-cyanophenylamino)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-1H-pyrazole-4-carboxylic acid benzyl ester

HRID 1161561Notes

Reaction equation

HRID 1161561 reaction equation
C[O:2][C:3](=O)[N:4]=[C:5](SC)[C:6]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[C:17]=1[F:36])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1.Cl.Cl.[CH2:42]([O:49][C:50]([C:52]1[CH:53]=[N:54][NH:55][C:56]=1[NH:57][NH2:58])=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.COC(=O)N=C(SC)C(C1C=C(OC)C=C(OCCCO[Si](C(C)(C)C)(C)C)C=1F)=NC1C=CC(C2N=C(C)ON=2)=CC=1.Cl.Cl.C(OC(C1C(NN)=NNC=1)=O)C>>[CH2:42]([O:49][C:50]([C:52]1[CH:53]=[N:54][NH:55][C:56]=1[N:57]1[C:3](=[O:2])[NH:4][C:5]([CH:6]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][Si:29]([C:32]([CH3:34])([CH3:33])[CH3:35])([CH3:31])[CH3:30])[C:17]=2[F:36])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]#[N:15])=[CH:12][CH:13]=2)=[N:58]1)=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 4

HCID 675040995-hydrazino-1H-pyrazole-4-carboxylic acid benzyl ester bishydrochlorideHCID 72312816(2-{3-[3-(t-Butyldimethylsilanyloxy)propoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl esterHCID 72312847(2-{3-[3-(t-Butyldimethylsilanyloxy)propoxy]-2-fluoro-5-methoxyphenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene)carbamic acid methyl esterHCID 178469938HCID 178469938, compound

Product 1

HCID 1359821055-{3-[{3-[3-(t-Butyldimethylsilanyloxy)propoxy]-2-fluoro-5-methoxyphenyl}-(4-cyanophenylamino)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-1H-pyrazole-4-carboxylic acid benzyl ester

Procedure

The same procedure was carried out as in Example (177b), except that (2-{3-[3-(t-butyldimethylsilanyloxy)propoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester (Example (163c)) and 5-hydrazino-1H-pyrazole-4-carboxylic acid benzyl ester bishydrochloride were used instead of respectively (2-{3-[3-(t-butyldimethylsilanyloxy)propoxy]-2-fluoro-5-methoxyphenyl}-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene)carbamic acid methyl ester and 3-hydrazino-1H-pyrazole-4-carboxylic acid ethyl ester bishydrochloride, to give the title compound as a light yellow solid.

Sources & evidence

ORD record
ord-0bcd3ca43d3a4f68a6efaf71c0b2aa43
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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