HCID 178466979, compound → HCID 178433885, compound

HRID 555620Notes

Reaction equation

HRID 555620 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([OH:16])=[C:14]([C:17](=O)[CH3:18])[C:13]([CH3:20])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[C:25]([C:26]2[CH:35]=[CH:34][C:29]([C:30]([NH:32][NH2:33])=[O:31])=[CH:28][CH:27]=2)=[N:24][N:23]=[N:22]1>Cl.CN(C=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14](=[C:17]([NH:33][NH:32][C:30](=[O:31])[C:29]3[CH:34]=[CH:35][C:26]([C:25]4[NH:24][N:23]=[N:22][N:21]=4)=[CH:27][CH:28]=3)[CH3:18])[C:13]([CH3:20])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 178466979HCID 178466979, compoundHCID 178514418HCID 178514418, compound

Product 1

HCID 178433885HCID 178433885, compoundYield 12.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

A DMF solution (1 ml) of 27.2 mg (0.10 mmol) of 1-(1-(4-tert-butylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl)-ethanone and 20.4 mg (0.10 mmol) of 4-(1H-tetrazol-5-yl)-benzoic hydrazide synthesized by the method disclosed in WO03/037328 was heated at 60° C. for 6 hours with one drop of concentrated hydrochloric acid, and the precipitated solid was washed with water and collected by filtration. The solid was mixed with 1M aqueous sodium hydroxide and filtered. 1M Hydrochloric acid was added to the filtrate, and the precipitated solid was collected by filtration to obtain 5.9 mg of the desired product as a brown solid (yield 12%).

Workup

  1. washthe precipitated solid was washed with water
  2. filtrationcollected by filtration
  3. additionThe solid was mixed with 1M aqueous sodium hydroxide
  4. filtrationfiltered
  5. addition1M Hydrochloric acid was added to the filtrate
  6. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-d0a6d0a2256f437bb85a3aa71904c89e
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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