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

HRID 2103898Notes

Reaction equation

HRID 2103898 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.[N+:21]([C:24]1[CH:33]=[C:32]([C:34]([NH:36][NH2:37])=[O:35])[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27])([O-:23])=[O:22].O.S(C1C=CC(C)=CC=1)(O)(=O)=O>>[OH:1][C:2]1[C:3]([C:18](=[N:37][NH:36][C:34]([C:32]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([N+:21]([O-:23])=[O:22])[CH:33]=2)=[O:35])[CH3:19])=[N:4][N:5]([CH3:17])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:16])[F:15])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 602067901-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanoneHCID 669863564-Methoxycarbonyl-3-nitrobenzhydrazide

Product 1

HCID 72359982methyl 4-{[2-(1-[4-hydroxy-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]ethylidene)hydrazino]carbonyl}-2-nitrobenzoateYield 60.7%

Procedure

From 1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone (0.70 mmol, 200 mg) synthesized in Synthetic Example 11, methyl 2-nitro-4-hydrazinocarbonylbenzoate (0.70 mmol, 168.3 mg) of Reference Synthetic Example 40 and tosylic acid monohydrate (36.4 mg, 0.21 mmol), 214.7 mg of the desired product was obtained in the same manner as in Synthetic Example 58 as a yellow solid (yield 60%).

Sources & evidence

ORD record
ord-c4970f3d47014070a11402fa22df71b3
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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