Water → HCID 24803339, compound

HRID 2353651Notes

Reaction equation

HRID 2353651 reaction equation
[CH:1]1([S:7][CH2:8][C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]3[CH3:21])[N:12]=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][CH3:32])=[O:30])=[CH:24][CH:23]=3)[N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:41])C=1.[Mn]([O-])(=O)(=O)=O.[Na+].[OH2:50]>O1CCOCC1>[CH:1]1([S:7]([CH2:8][C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]3[CH3:21])[N:12]=[C:11]([C:22]3[CH:23]=[CH:24][C:25]([NH:28][C:29]([NH:31][CH3:32])=[O:30])=[CH:26][CH:27]=3)[N:10]=2)(=[O:41])=[O:50])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acid3×HCID 23673458Sodium Permanganate3×HCID 59379929HCID 59379929, compound

Product 1

HCID 24803339HCID 24803339, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-[4-[4-(Cyclohexylsulfanylmethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methyl-urea (0.35 mmol) was dissolved in 1,4-dioxane (5 mL) and water (1 mL). 3-chloroperbenzoic acid (75%) (121 mg) was added to the solution followed immediately by sodium permanganate (140 mg) and the reactions stirred at RT for 1 hour. Further 3-chloroperbenzoic acid (75%) (121 mg) and sodium permanganate (140 mg) were added and the reactions allowed to stir at RT for 1 hour. Further 3-chloroperbenzoic acid (75%) (121 mg) and sodium permanganate (140 mg) were added and the reactions allowed to stir at RT for another 1 hour then loaded onto a SCX-3 column. The column was washed with methanol and the desired material removed with 7N ammonia in methanol. The crude material was purified by prep-HPLC (basic) to give the desired material (74 mg) as a white solid.

Workup

  1. stirringto stir at RT for 1 hour
  2. stirringto stir at RT for another 1 hour
  3. washThe column was washed with methanol
  4. customthe desired material removed with 7N ammonia in methanol
  5. customThe crude material was purified by prep-HPLC (basic)

Sources & evidence

ORD record
ord-ab61751fc55745ef825ba9b1773cb07b
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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