Triethylamine → 6-(3-{[2-Fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)pyridine-2-carboxylic acid methyl ester
Reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][NH2:13])[N:7]=1)=[O:5].C(N(CC)CC)C.C[O:22][C:23](=O)[N:24]=[C:25](SC)[C:26]([C:40]1[CH:45]=[C:44]([O:46][CH3:47])[CH:43]=[C:42]([O:48][CH2:49][CH2:50][F:51])[C:41]=1[F:52])=[N:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:38]=[C:37]([CH3:39])[O:36][N:35]=2)=[CH:30][CH:29]=1>CN(C=O)C>[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]2[C:23](=[O:22])[NH:24][C:25]([CH:26]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[CH:43]=[C:42]([O:48][CH2:49][CH2:50][F:51])[C:41]=3[F:52])[NH:27][C:28]3[CH:29]=[CH:30][C:31]([C:34]4[N:38]=[C:37]([CH3:39])[O:36][N:35]=4)=[CH:32][CH:33]=3)=[N:13]2)[N:7]=1)=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
After adding 149 mg of 6-hydrazinopyridine-2-carboxylic acid methyl ester hydrochloride and 92 μl of triethylamine to a solution of 255 mg of {2-[2-fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (3e)) in 5 ml of DMF, the mixture was stirred at 85° C. for 24 hours under a nitrogen atmosphere.
Sources & evidence
- ORD record
- ord-3f17a2313ac641eb8842869c4bbb9b7c
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816522B2
Reaction notes
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