Sodium Hydroxide → (6-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-benzo[b]thiophen-3-yl)-acetic acid

HRID 2261868Notes

Reaction equation

HRID 2261868 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][C:6]1[C:7]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4[N:24]([C:31]5[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=5[Cl:38])[N:25]=[CH:26][C:27]=4[CH:28]([CH3:30])[CH3:29])=[CH:17][C:16]=3[CH3:39])=[CH:11][C:8]=2[S:9][CH:10]=1)C.[OH-].[Na+]>O1CCCC1.CO>[Cl:37][C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:38])[C:31]=1[N:24]1[C:23]([CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:15]([C:12]3[CH:13]=[CH:14][C:7]4[C:6]([CH2:5][C:4]([OH:40])=[O:3])=[CH:10][S:9][C:8]=4[CH:11]=3)=[C:16]([CH3:39])[CH:17]=2)=[C:27]([CH:28]([CH3:30])[CH3:29])[CH:26]=[N:25]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67527663HCID 67527663, compound

Product 1

HCID 57443371(6-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-benzo[b]thiophen-3-yl)-acetic acidYield 68.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6-{4-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (43 mg; 0.072 mmoles) in tetrahydrofuran (1.0 mL) and methanol (1.0 mL) is treated with sodium hydroxide (1.0 mL; 1.0 N). The mixture is stirred at room temperature for 2 hours and quenched with HCl (1.0 mL, 1.0 M). The mixture is extracted with EtOAc (10 mL×2). The combined organic layers are dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography (eluting with 30-100% EtOAc/Hexanes) and the appropriate fractions are concentrated. The material is dried in vacuo to afford the title compound (28 mg, 68%). ES/MS m/e 564.8; 566.8 (M+1); 562.8; 564.8 (M−1)

Workup

  1. customquenched with HCl (1.0 mL, 1.0 M)
  2. extractionThe mixture is extracted with EtOAc (10 mL×2)
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by flash chromatography (eluting with 30-100% EtOAc/Hexanes)
  7. concentrationthe appropriate fractions are concentrated
  8. customThe material is dried in vacuo

Sources & evidence

ORD record
ord-d28943856c544b42b81f451eab27c618
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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