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Sodium Bicarbonate → 3-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)pyridin-2-yl methanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid sodium salt

HRID 2182841
Notes
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Reaction equation

HRID 2182841 reaction equation
[N+](C1C=C(S(CC[O:15][C:16](=[O:51])[C:17]2[CH:22]=[CH:21][CH:20]=[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])[CH:18]=2)(=O)=O)C=CC=1)([O-])=O.C([O-])(O)=O.[Na+:56]>C1COCC1.O>[Na+:56].[CH3:44][C:43]1[C:38]([CH2:37][S:35]([C:27]2[N:26]([S:23]([C:19]3[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=3)[C:16]([O-:51])=[O:15])(=[O:25])=[O:24])[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:50])([F:48])[F:49]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 207863723-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}benzoic Acid 2-(3-nitro-benzenesulfonyl)ethyl Ester2×

Product 1

HCID 695572403-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)pyridin-2-yl methanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid sodium saltYield 94%

Reagents, catalysts & solvents 1

HCID 21881883
Oxolane--water (1/1)
Solvent

Procedure

A solution of 3-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-benzoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester (Intermediate 2, 900 mg, 1.17 mmol) and NaHCO3 (118 mg, 1.41 mmol, 1.2 eq.) in THF-H2O (6 mL-3 mL) was heated to 70° C. for 20 min, during which time the heterogeneous mixture became clear. Thereafter all the volatile materials were removed in vacuo, the residual gummy material was dissolved in CH2Cl2, and the mixture was filtered to remove solids. The filtrate was evaporated to dryness in vacuo, and the residual yellow foam was treated with ether-EtOAc (5:1) to precipitate a solid. This solid was collected by filtration to give 630 mg (94%) of 3-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)pyridin-2-yl methanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid sodium salt (sodium salt of Compound 1).

Workup

  1. customThereafter all the volatile materials were removed in vacuo
  2. dissolutionthe residual gummy material was dissolved in CH2Cl2
  3. filtrationthe mixture was filtered
  4. customto remove solids
  5. customThe filtrate was evaporated to dryness in vacuo
  6. additionthe residual yellow foam was treated with ether-EtOAc (5:1)
  7. customto precipitate a solid
  8. filtrationThis solid was collected by filtration

Sources & evidence

ORD record
ord-9f19678286ca408bbec4c9851fc38780
Source dataset
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06897227B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes