Sodium Thiosulfate → HCID 56851052, compound

HRID 1786992Notes

Reaction equation

HRID 1786992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][S:31][CH2:32][CH2:33][OH:34])[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.ClC1C=CC=C(C(OO)=[O:43])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][S:31]([CH2:32][CH2:33][OH:34])=[O:43])[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 56851051HCID 56851051, compound

Product 1

HCID 56851052HCID 56851052, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-({2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}thio)ethanol (100 mg) in dichloromethane (10 mL) was added dropwise a 70% solution of 3-chloroperbenzoic acid (58 mg) in dichloromethane (5.0 mL) at −78° C. The mixture was stirred at −78° C. for 1 hr, and aqueous sodium thiosulfate solution was added. After stirring at room temperature for 0.5 hr, the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine and dried over magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate→ethyl acetate:methanol=4:1) to give the title compound (87 mg) as colorless crystals.

Workup

  1. stirringAfter stirring at room temperature for 0.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography (eluent, ethyl acetate→ethyl acetate:methanol=4:1)

Sources & evidence

ORD record
ord-7bf0f327fdc04e4c84fb4419c62b0309
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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