Sodium Thiosulfate → HCID 69522600, compound

HRID 856528Notes

Reaction equation

HRID 856528 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:50]=[CH:49][C:35]5[N:36]=[C:37]([S:39][CH2:40][C:41]6[N:45]([CH2:46][CH2:47][CH3:48])[CH:44]=[N:43][CH:42]=6)[NH:38][C:34]=5[CH:33]=4)=[O:30])=[CH:20][C:19]=3[CH:51]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:60])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:23][CH2:22][C:21]([C:29]([NH:31][C:32]4[CH:50]=[CH:49][C:35]5[N:36]=[C:37]([S:39]([CH2:40][C:41]6[N:45]([CH2:46][CH2:47][CH3:48])[CH:44]=[N:43][CH:42]=6)=[O:60])[NH:38][C:34]=5[CH:33]=4)=[O:30])=[CH:20][C:19]=3[CH:51]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 69522335HCID 69522335, compound

Product 1

HCID 69522600HCID 69522600, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[2-[[(1-propylimidazol-5-yl)methyl]sulfanyl]benzimidazol-5-yl]-2,3-dihydro-1-benzazepine-4-carboxamide (0.64 g) was dissolved in methylene chloride (19.2 ml), and a solution of metachloroperbenzoic acid (0.27 g) in methylene chloride (12.8 ml) was added dropwise to the solution at −78° C. The mixture was stirred for 15 minutes, and to the mixture was added an aqueous solution of saturated sodium thiosulfate, and the mixture was allowed to be warmed to room temperature. The mixture was extracted with ethyl acetate, washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[2-[[(1-propylimidazol-5-yl)methyl]sulfinyl]benzimidazol-5-yl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 313) (0.21 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1c20b538cf6c4cb2a7867462aaa8ea87
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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