Hydrochloric Acid → HCID 59633213, compound

HRID 2369049Notes

Reaction equation

HRID 2369049 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]([C:16]3[N:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[Cl:31])[N:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=3)=[CH:14][CH:15]=2)=[C:7]([CH3:32])[CH:6]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[N:17]1[C:16]([C:13]2[S:12][C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:33])=[O:2])=[CH:6][C:7]=3[CH3:32])=[CH:15][CH:14]=2)=[CH:20][C:19]([C:21]([F:24])([F:22])[F:23])=[N:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59633255HCID 59633255, compound

Product 1

HCID 59633213HCID 59633213, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4-{5-[2-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-thiophen-2-yl}-3-methylphenyl)-acetic acid methyl ester (122 mg, 025 mmol) was dissolved in 6 mL mixture of THF and water (3:1, V/V). Lithium hydroxide monohydrate (23 mg, 0.55 mmol) was then added. After stirring at room temperature for 2 hrs, the mixture was neutralized to pH 7 by 1N HCl, and then extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by reverse HPLC to give a white solid (66 mg, 55% yield). 1H-NMR (400 MHz, CDCl3): δ 2.33 (s, 3H), 3.65 (s, 2H), 6.88-6.84 (m, 3H), 7.17-7.11 (m, 1H), 7.17 (m, 1H), 7.27 (m, 1H), 7.56-7.42 (m, 4H). MS (ES) 477.2, [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by reverse HPLC

Sources & evidence

ORD record
ord-7df25bdef3c4483a99cae8ce532b4986
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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