Hydrochloric Acid → 5-{1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic Acid 2-methoxyethylamide

HRID 2422808Notes

Reaction equation

HRID 2422808 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.[CH3:21][O:22][CH2:23][CH2:24][NH:25][C:26]([C:28]1[S:29][C:30]([C:33]([NH:35][NH2:36])=[O:34])=[CH:31][CH:32]=1)=[O:27].Cl.O>CN(C)C=O>[CH3:21][O:22][CH2:23][CH2:24][NH:25][C:26]([C:28]1[S:29][C:30]([C:33]([NH:35][N:36]=[C:18]([C:3]2[C:2]([OH:1])=[C:6]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=3)[N:5]([CH3:17])[N:4]=2)[CH3:19])=[O:34])=[CH:31][CH:32]=1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 576881845-Hydrazinocarbonylthiophene-2-carboxylic acid 2-methoxyethylamideHCID 602067901-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone

Product 1

HCID 765978465-{1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic Acid 2-methoxyethylamideYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone (50 mg, 0.18 mmol) and 5-hydrazinocarbonylthiophene-2-carboxylic acid 2-methoxyethylamide (64 mg, 0.26 mmol) prepared in Reference Synthetic Example 5 in dimethylformamide (0.88 mL), concentrated hydrochloric acid (15 μL, 0.18 mmol) was added at room temperature, and the resulting mixture was stirred for 15 hours. After the reaction, water was added, and the resulting crystals were recovered by filtration and dried. Chloroform was added, and the resulting crystals were recovered by filtration to give 59 mg of the desired product (yield 66%).

Workup

  1. additionwas added
  2. filtrationthe resulting crystals were recovered by filtration
  3. customdried
  4. additionChloroform was added
  5. filtrationthe resulting crystals were recovered by filtration

Sources & evidence

ORD record
ord-2e444db214c4461ea6f4547b90074489
Source dataset
uspto-grants-2011_06
Patent number
US07960425B2

Reaction notes

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