Hydrochloric Acid → HCID 10116542, compound

HRID 1357226Notes

Reaction equation

HRID 1357226 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:37])[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:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)[C:26]=3[CH2:27][CH2:28][CH3:29])=[O:21])[CH:14]=2)[CH:9]=1.O.Cl>CO>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([N:25]2[C:26]([CH2:27][CH2:28][CH3:29])=[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:37])=[O:4])[CH:17]=[CH:16]4)=[O:21])[CH:23]=[N:24]2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69137761HCID 69137761, compound

Product 1

HCID 10116542HCID 10116542, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N NaOH (335 μL, 0.335 mmol) was added under nitrogen to a solution of [6-({[1-(4-chloro-phenyl)-5-propyl-1H-pyrazole-4-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-acetic acid methyl ester (150 mg, 0.305 mmol), prepared in the previous step, in 25 mL of MeOH plus 10 mL of water at room temperature. After the addition the reaction was stirred at room temperature for 20 h (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 (138 mg, 94%) as a pink solid, mp 203-204° 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-bad7ebda1bc043f5a6df3e90ad94bea7
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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