Sodium Thiosulfate → HCID 66599927, compound

HRID 1811968Notes

Reaction equation

HRID 1811968 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[CH:14][C:13]([CH:16]([C:18]3[CH:23]=[CH:22][C:21](SC)=[CH:20][CH:19]=3)[OH:17])=[CH:12][C:11]=2[C:26]2[N:34]=[C:33]([CH3:35])[N:32]=[C:31]3[C:27]=2[N:28]=[CH:29][N:30]3[CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)=[CH:5][CH:4]=1.[CH:42]1C=C(Cl)C=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+].[S:58]([O-:62])([O-])(=[O:60])=S.[Na+].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[CH:14][C:13]([CH:16]([C:18]3[CH:23]=[CH:22][C:21]([S:58]([CH3:42])(=[O:62])=[O:60])=[CH:20][CH:19]=3)[OH:17])=[CH:12][C:11]=2[C:26]2[N:34]=[C:33]([CH3:35])[N:32]=[C:31]3[C:27]=2[N:28]=[CH:29][N:30]3[CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid3×HCID 516892Sodium BicarbonateHCID 66600055HCID 66600055, compound

Product 1

HCID 66599927HCID 66599927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)(4-(methylthio)phenyl)methanol (241 mg, 0.423 mmol) was dissolved in DCM (4.0 mL) and the reaction flask was cooled in an ice water bath under nitrogen. Then, mCPBA (180.5 mg, 1.046 mmol) was added as a solution in DCM (5 mL) via syringe, and the reaction was warmed to room temperature and stirred. After 45 min, more mCPBA (58 mg, 0.34 mmol) was added, and stirring was continued. After 25 min, more mCPBA (27.3 mg, 0.158 mmol) was added, and stirring was continued. After 15 minutes, the reaction was treated with a solution made of 10 mL saturated sodium bicarbonate and 2 mL saturated sodium thiosulfate. The mixture was stirred at room temperature for 30 min. Then, the layers were separated and the aqueous phase was extracted with DCM and then with 10:1 DCM/MeOH. The organic extracts were combined, washed with brine, concentrated, and dried under high vacuum in a water bath (about 40° C.) to give (6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)(4-(methylsulfonyl)phenyl)methanol, which was taken on directly to the next step. 1H NMR (CDCl3, 400 MHz) δ 12.54 (s, 1H), 9.75 (s, 1H), 8.40 (s, 1H), 8.27-8.21 (m, 2H), 8.17 (d, J=8.22 Hz, 1H), 7.95-7.89 (m, 2H), 7.74-7.68 (m, 2H), 6.78 (d, J=10.17 Hz, 1H), 6.01 (s, 1H), 5.85 (d, J=11.93 Hz, 1H), 4.21 (d, J=13.11 Hz, 1H), 3.95 (s, 3H), 3.87-3.77 (m, 1H), 3.03 (s, 3H), 2.97-2.89 (m, 1H), 2.89 (s, 3H), 2.19-1.95 (m, 3H), 1.93-1.65 (m, 3H). m/z (ESI, +ve ion) 602 (M+H)+.

Workup

  1. temperaturethe reaction flask was cooled in an ice water bath under nitrogen
  2. stirringstirring
  3. waitAfter 25 min
  4. stirringstirring
  5. waitAfter 15 minutes
  6. additionthe reaction was treated with a solution
  7. stirringThe mixture was stirred at room temperature for 30 min
  8. customThen, the layers were separated
  9. extractionthe aqueous phase was extracted with DCM
  10. washwashed with brine
  11. concentrationconcentrated
  12. customdried under high vacuum in a water bath (about 40° C.)

Sources & evidence

ORD record
ord-1c1338daee3e4be3812461ae1b833c99
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

Loading…