Water → HCID 59380182, compound

HRID 2353681Notes

Reaction equation

HRID 2353681 reaction equation
[CH3:1][NH:2][C:3](=[O:32])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([CH2:17][S:18][C:19]3[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=3)[CH:14]=[C:13]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]3[CH3:31])[N:12]=2)=[CH:7][CH:6]=1.C1C=C(Cl)C=C(C(OO)=[O:41])C=1.[Mn]([O-])(=O)(=O)=O.[Na+].[OH2:50]>O1CCOCC1>[CH3:1][NH:2][C:3](=[O:32])[NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[C:15]([CH2:17][S:18]([C:19]3[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=3)(=[O:41])=[O:50])[CH:14]=[C:13]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]3[CH3:31])[N:12]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 23673458Sodium PermanganateHCID 59380165HCID 59380165, compound

Product 1

HCID 59380182HCID 59380182, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Methyl-1-[4-[4-[(1-methylimidazol-2-yl)sulfanylmethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea (0.23 mmol) was dissolved in 1,4-Dioxane (4 mL) and water (1 mL). m-CPBA (75%) (80 mg), followed immediately by sodium permanganate (92 mg), was added to the solution. The reaction was allowed to stir at RT for 18 h then loaded onto a SCX-2 (10 g) column, which was washed with methanol and the product eluted with 7N ammonia in methanol. The reaction was vacuumed to dryness and purified by prep-HPLC (basic) to give the desired material (37 mg) as a white solid.

Workup

  1. additionwas added to the solution
  2. washwas washed with methanol
  3. washthe product eluted with 7N ammonia in methanol
  4. custompurified by prep-HPLC (basic)

Sources & evidence

ORD record
ord-cb18d55037c54762931a4f637852934d
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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