Water → HCID 10301697, compound

HRID 1357230Notes

Reaction equation

HRID 1357230 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:16][NH:17][C:18]([C:20]3[CH:21]=[N:22][N:23]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:24]=3[CH2:25][CH2:26][CH3:27])=[O:19])[CH:12]=2)[C:7]=1[Br:34].[OH-].[Na+].O>CO>[Br:34][C:7]1[C:8]2[C:13](=[CH:12][C:11]([CH2:16][NH:17][C:18]([C:20]3[CH:21]=[N:22][N:23]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:24]=3[CH2:25][CH2:26][CH3:27])=[O:19])=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[O:5][CH2:4][C:3]([OH:35])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 69138517HCID 69138517, compound

Product 1

HCID 10301697HCID 10301697, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (1-bromo-6-{[(1-phenyl-5-propyl-1H-pyrazole-4-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-acetic acid methyl ester (0.20 g, 0.373 mmol), prepared in the previous step, 1N NaOH (373 μL, 0.373 mmol), 5 mL of water and 60 mL of methanol was stirred at room temperature for 20 h. Starting material was present by TLC. An additional 186 μL (0.186 mmol) of 1N NaOH was added and the reaction stirred at room temperature for 18 h. The reaction was filtered to remove trace solids and acidified with 1N HCl until pH 1 by litmus paper. The methanol was removed under reduced pressure. The solid formed was collected by filtration and dried under reduced pressure to give the title compound (0.13 g, 67%) as an off-white solid, mp 140-145° C.

Workup

  1. stirringthe reaction stirred at room temperature for 18 h
  2. filtrationThe reaction was filtered
  3. customto remove trace solids
  4. customThe methanol was removed under reduced pressure
  5. customThe solid formed
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-137dbd9283114a36ba3fbd93f19489b4
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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