Sodium Bicarbonate → 4-[2-{3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl}-benzimidazole-1-sulfonyl]-3-isopropyl-5-methylphenoxyacetic acid sodium salt

HRID 2182888Notes

Reaction equation

HRID 2182888 reaction equation
C1(C)C=CC(S(CC[O:12][C:13](=[O:54])[CH2:14][O:15][C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([S:23]([N:26]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[N:28]=[C:27]3[S:35]([CH2:37][C:38]3[C:43]([CH3:44])=[C:42]([O:45][CH2:46][C:47]([F:50])([F:49])[F:48])[CH:41]=[CH:40][N:39]=3)=[O:36])(=[O:25])=[O:24])=[C:18]([CH:51]([CH3:53])[CH3:52])[CH:17]=2)(=O)=O)=CC=1.C([O-])(O)=O.[Na+:60]>CC#N.O>[Na+:60].[CH3:44][C:43]1[C:38]([CH2:37][S:35]([C:27]2[N:26]([S:23]([C:19]3[C:20]([CH3:22])=[CH:21][C:16]([O:15][CH2:14][C:13]([O-:54])=[O:12])=[CH:17][C:18]=3[CH:51]([CH3:53])[CH3:52])(=[O:24])=[O:25])[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[N:28]=2)=[O:36])=[N:39][CH:40]=[CH:41][C:42]=1[O:45][CH2:46][C:47]([F:49])([F:48])[F:50]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 207864214-[2-{3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl}-benzimidazole-1-sulfonyl]-3-isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester2×

Product 1

HCID 207863674-[2-{3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl}-benzimidazole-1-sulfonyl]-3-isopropyl-5-methylphenoxyacetic acid sodium saltYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-[2-{3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl}-benzimidazole-1-sulfonyl]-3-isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 68, 1.6 g, 1.95 mmol) in 15 mL of CH3CN was added the solution of NaHCO3 (200 mg, 2.34 mmol, 1.2 eq) in 8 mL of H2O. The mixture was heated to 65° C. for 1.5 h. Thereafter all volatile materials were removed under vacuum, the mixture was washed with ether (2×), and then the aqueous layer was lyophilized overnight. The solid was dissolved in 110 mL of ether-EtOAc (10:1), and then the mixture was filtered to remove insoluble material. The filtrate was concentrated and the residual oil was dissolved in 10 mL of ether-EtOAc (10:1). Hexane was added to the mixture to precipitate a white solid. The precipitate was filtered, washed with hexane, and dried under vacuum to yield 1.0 g (77%) of 4-[2-{3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl}-benzimidazole-1-sulfonyl]-3-isopropyl-5-methylphenoxyacetic acid sodium salt (Compound 39) as a white solid.

Workup

  1. customThereafter all volatile materials were removed under vacuum
  2. washthe mixture was washed with ether (2×)
  3. dissolutionThe solid was dissolved in 110 mL of ether-EtOAc (10:1)
  4. filtrationthe mixture was filtered
  5. customto remove insoluble material
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe residual oil was dissolved in 10 mL of ether-EtOAc (10:1)
  8. additionHexane was added to the mixture
  9. customto precipitate a white solid
  10. filtrationThe precipitate was filtered
  11. washwashed with hexane
  12. customdried under vacuum

Sources & evidence

ORD record
ord-cae9820319da480ba75335094bf2f76e
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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