Hydrochloric Acid → 3-Methoxybenzoic Acid

HRID 130496

Reaction equation

HRID 130496 reaction equation
FC1C=C(C2C=CC=CC=2S(C)(=O)=O)C=CC=1NC(C1N([C:16]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:17]=2[C:18]([OH:20])=[O:19])N=C(C(F)(F)F)C=1)=O.COC(=O)C1C=C(OC)C=CC=1N1C(C(=O)NC2C=CC(C3C=CC=CC=3S(C)(=O)=O)=CC=2F)=CC(C(F)(F)F)=N1.[OH-].[Na+].Cl>CO.O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][CH:16]=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 586301122-[5-(3-Fluoro-2'-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxy-benzoic acidHCID 586302552-[5-(3-Fluoro-2'-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxybenzoic acid methyl ester

Product 1

HCID 114613-Methoxybenzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Part D: Preparation of 2-[5-(3-Fluoro-2′-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxy-benzoic acid. 2-[5-(3-Fluoro-2′-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxybenzoic acid methyl ester (1.70 g, 2.80 mmol) was dissolved in methanol (22 mL), 1N sodium hydroxide (5.8 mL) was added, and the solution refluxed for 6 hours. The reaction was cooled to ambient temperature and diluted with water (30 mL). 3N hydrochloric acid was added to adjust the pH to 2, and the resulting precipitate collected by filtration. The solid was dried under vacuum in a desiccator to give 1.45 g (86%) of (3-fluoro-2′-methanesulfonyl-biphenyl-4-ylcarbamoyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methoxy-benzoic acid. 1H NMR (CD3OD) δ 8.12 (dd, J=1.5, 8.1 Hz, 1H), 7.86 (t, J=8.4 Hz, 1H), 7.70 (dt, J=1.5, 7.7 Hz, 1H), 7.61 (dt, J=1.5, 7.7 Hz, 1H), 7.37 (m, 3H), 7.25 (dd, J=2.2, 11.7 Hz, 1H) 7.16 (m, 3H) 3.87 (s, 3H), 2.67 (s, 3H).

Workup

  1. temperaturethe solution refluxed for 6 hours
  2. filtrationthe resulting precipitate collected by filtration
  3. customThe solid was dried under vacuum in a desiccator

Sources & evidence

ORD record
ord-cae83c570c1247afa1f0b18e7dd23a20
Source dataset
uspto-grants-2008_06
Patent number
US07381732B2

Linked notes

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