Sodium Thiosulfate → HCID 71612145, compound

HRID 1484696Notes

Reaction equation

HRID 1484696 reaction equation
[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:15]([F:16])=[CH:14][C:13]([O:17][CH2:18][CH3:19])=[CH:12][C:11]=3[F:20])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[C:24]([O:34][CH2:35][CH2:36][S:37][CH3:38])=[CH:23][N:22]=3)[C:5]=2[CH3:39])[CH2:3][CH2:2]1.ClC1C=C(C(OO)=[O:48])C=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[CH:1]1([C:4]2[N:8]([CH2:9][C:10]3[C:15]([F:16])=[CH:14][C:13]([O:17][CH2:18][CH3:19])=[CH:12][C:11]=3[F:20])[N:7]=[C:6]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=4)[C:24]([O:34][CH2:35][CH2:36][S:37]([CH3:38])=[O:48])=[CH:23][N:22]=3)[C:5]=2[CH3:39])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 71611599HCID 71611599, compound

Product 1

HCID 71612145HCID 71612145, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

180 mg 2-[5-cyclopropyl-1-(4-ethoxy-2,6-difluorobenzyl)-4-methyl-1H-pyrazol-3-yl]-5-[2-(methylsulfanyl)ethoxy]-N-(pyridin-4-yl)pyrimidin-4-amine (0.326 mmol, 1.0 eq.) were dissolved in 1.7 mL chloroform and cooled to 0° C. 80.3 mg 3-chlorobenzenecarboperoxoic acid and the reaction mixture was stirred at 0° C. for 30 minutes. The reaction mixture was diluted with DCM and a solution of sodium thiosulfate (10% in water) was added and stirred for 5 minutes. The layers were separated and the aqueous layer was washed with DCM twice. The combined organic layers were washed with saturated sodium hydrogencarbonate solution, was dried over a silicon filter and concentrated in vacuo. The crude product was purified by flash chromatography to provide 136 mg of the analytically pure target compound as a racemate.

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed with DCM twice
  3. washThe combined organic layers were washed with saturated sodium hydrogencarbonate solution
  4. customwas dried over a silicon
  5. filtrationfilter
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography
  8. customto provide 136 mg of the analytically pure target compound as a racemate

Sources & evidence

ORD record
ord-3e5d5b8d6b57459282a323aba3368f39
Source dataset
uspto-grants-2016_08
Patent number
US09422268B2

Reaction notes

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