Sodium Thiosulfate → HCID 60155988, compound

HRID 1811973Notes

Reaction equation

HRID 1811973 reaction equation
[F:1][C:2]1[C:7]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:9]=2)=[CH:6][C:5]([CH2:34][C:35]2[CH:40]=[CH:39][C:38](SC)=[CH:37][CH:36]=2)=[CH:4][N:3]=1.[CH:43]1C=C(Cl)C=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+].[S:59]([O-:63])([O-])(=[O:61])=S.[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[C:7]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)[N:9]=2)=[CH:6][C:5]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([S:59]([CH3:43])(=[O:63])=[O:61])=[CH:39][CH:40]=2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 60155987HCID 60155987, compound

Product 1

HCID 60155988HCID 60155988, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(2-Fluoro-5-(4-(methylthio)benzyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (624.5 mg, 1.074 mmol) was dissolved in DCM (11 mL) and the flask was cooled in an ice water bath. Then, mCPBA (557 mg, 3.23 mmol) was added as a solution in DCM (17.5 mL) and the reaction was warmed to room temperature and stirred under nitrogen. After 35 min, the reaction was treated with a mixture of saturated sodium bicarbonate (25 mL) and saturated sodium thiosulfate (6 mL), and stirring was continued at room temperature. After 50 minutes, the layers were separated, and the aqueous phase was extracted with DCM. The organic phase was dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter (30 mL fritted filter with about 1 inch of silica gel; DCM to 50:1 DCM/MeOH) to give 4-(2-fluoro-5-(4-(methylsulfonyl)benzyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (539.6 mg, 75% yield based on 91% purity). 1H NMR (CDCl3, 400 MHz) δ 8.34 (dd, J=8.90 Hz, 2.45 Hz, 1H), 8.16 (d, J=1.76 Hz, 1H), 7.89 (d, J=8.41 Hz, 2H), 7.40 (d, J=8.22 Hz, 2H), 7.21 (d, J=8.61 Hz, 4H), 6.90-6.82 (m, 4H), 4.82 (s, 2H), 4.79 (s, 2H), 4.13 (s, 2H), 3.82 (s, 3H), 3.80 (s, 3H), 3.03 (s, 3H), 2.54 (s, 3H). m/z (ESI, +ve ion) m/z 614 (M+H)+.

Workup

  1. temperaturethe flask was cooled in an ice water bath
  2. stirringstirring
  3. customwas continued at room temperature
  4. waitAfter 50 minutes
  5. customthe layers were separated
  6. extractionthe aqueous phase was extracted with DCM
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified on a silica gel
  11. filtrationfilter (30 mL fritted filter with about 1 inch of silica gel; DCM to 50:1 DCM/MeOH)

Sources & evidence

ORD record
ord-ae45f03302164569859810e9541dcb5b
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

Loading…