p-Toluenesulfonic acid monohydrate → methyl 5-{[2-(1-{4-hydroxy-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}ethylidene)hydrazino]carbonyl}-2-thiophenecarboxylate

HRID 1881634Notes

Reaction equation

HRID 1881634 reaction equation
[OH:1][C:2]1[C:3]([C:18](=O)[CH3:19])=[N:4][N:5]([CH3:17])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[NH:21]([C:23]([C:25]1[S:29][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][CH:26]=1)=[O:24])[NH2:22].O.S(C1C=CC(C)=CC=1)(O)(=O)=O>>[OH:1][C:2]1[C:3]([C:18](=[N:22][NH:21][C:23]([C:25]2[S:29][C:28]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][CH:26]=2)=[O:24])[CH3:19])=[N:4][N:5]([CH3:17])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 148719615-Methoxycarbonyl-2-thiophenecarboxylic acid hydrazideHCID 602067901-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone

Product 1

HCID 72360041methyl 5-{[2-(1-{4-hydroxy-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}ethylidene)hydrazino]carbonyl}-2-thiophenecarboxylateYield 57.6%

Procedure

From 1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone (200 mg, 0.70 mmol) synthesized in Synthetic Example 11, methyl 5-hydrazinocarbonyl-2-thiophenecarboxylate (0.70 mmol, 140.9 mg) of Reference Synthetic Example 39 and tosylic acid monohydrate (36.4 mg, 0.21 mmol), 188.2 mg of the desired product was obtained in the same manner as in Synthetic Example 58 as a pale yellow solid (yield 57%).

Sources & evidence

ORD record
ord-7a5e0ad06bd9421088855352d7bde38e
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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