Water → HCID 59379885, compound

HRID 2353676Notes

Reaction equation

HRID 2353676 reaction equation
[CH3:1][NH:2][C:3](=[O:31])[CH2:4][S:5][CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]2[CH3:19])[N:10]=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:30])[NH:28][CH3:29])=[CH:22][CH:21]=2)[N:8]=1.C1C=C(Cl)C=C(C(OO)=[O:40])C=1.[Mn]([O-])(=O)(=O)=O.[Na+].[OH2:49]>O1CCOCC1>[CH3:1][NH:2][C:3](=[O:31])[CH2:4][S:5]([CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]2[CH3:19])[N:10]=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:30])[NH:28][CH3:29])=[CH:22][CH:21]=2)[N:8]=1)(=[O:40])=[O:49]

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acid3×HCID 23673458Sodium Permanganate3×HCID 59379949HCID 59379949, compound

Product 1

HCID 59379885HCID 59379885, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-Methyl-2-[[2-[4-(methylcarbamoylamino)phenyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methylsulfanyl]acetamide (0.35 mmol) was dissolved in 1,4-Dioxane (5 mL) and water (1 mL). m-CPBA (75%) (121 mg) followed immediately by sodium permanganate (140 mg) were added to the solution and the reaction stirred at RT for 1 h. Further m-CPBA (75%) (121 mg) followed immediately by sodium permanganate (140 mg) were added to the solution and stirred at RT for 1 h. Again further m-CPBA (75%) (121 mg) followed immediately by sodium permanganate (140 mg) were added and the reaction stirred at RT for 1 h. The reaction was loaded onto a SCX-3 (10 g) column, which was washed with methanol and the product eluted with 7N ammonia in methanol. The material was further purified by prep-HPLC (basic) to give the desired material (30 mg) as a white solid.

Workup

  1. additionwere added to the solution
  2. additionwere added to the solution
  3. stirringstirred at RT for 1 h
  4. additionwere added
  5. stirringthe reaction stirred at RT for 1 h
  6. washwas washed with methanol
  7. washthe product eluted with 7N ammonia in methanol
  8. customThe material was further purified by prep-HPLC (basic)

Sources & evidence

ORD record
ord-624bf72d91cc41b081bc71e7d1869425
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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