Hydrochloric Acid → HCID 10118010, compound

HRID 1357227Notes

Reaction equation

HRID 1357227 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:38])[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][NH:19][C:20]([C:22]3[CH:23]=[N:24][N:25]([C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=4)[C:26]=3[C:27]([F:30])([F:29])[F:28])=[O:21])[CH:14]=2)[CH:9]=1.O.Cl>CO>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([N:25]2[C:26]([C:27]([F:30])([F:29])[F:28])=[C:22]([C:20]([NH:19][CH2:18][C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[CH:9]=[C:8]([O:7][CH2:6][C:5]([OH:38])=[O:4])[CH:17]=[CH:16]4)=[O:21])[CH:23]=[N:24]2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69137745HCID 69137745, compound

Product 1

HCID 10118010HCID 10118010, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N NaOH (563 μL, 0.563 mmol) was added under nitrogen to [6-({[1-(4-chloro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-acetic acid methyl ester (243 mg, 0.469 mmol), prepared in the previous step, in 100 mL of MeOH plus 25 mL of water at room temperature. After the addition the reaction was stirred at room temperature overnight. The reaction was acidified by the addition of 1 N HCl and then concentrated under reduced pressure to remove the MeOH. The solid present was collected by filtration and dried under reduced pressure to give the title compound (210 mg, 89%) as a pink solid, mp 189-191° C.

Workup

  1. customat room temperature
  2. additionAfter the addition the reaction
  3. concentrationconcentrated under reduced pressure
  4. customto remove the MeOH
  5. filtrationThe solid present was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-619ba2286b25438fae21bcc1a9176783
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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