Hydrogen Peroxide → HCID 86695194, compound

HRID 1504034Notes

Reaction equation

HRID 1504034 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([CH:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]4[C:26]=3[C:25]3[C@@H:24]([CH2:27][C:28]#[N:29])[CH2:23][CH2:22][C:21]=3[S:20]4)[CH2:10][CH2:9]2)[CH2:3]1.[OH:30][Li].O.OO>CO>[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([CH:8]2[CH2:9][CH2:10][CH:11]([O:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]4[C:26]=3[C:25]3[C@@H:24]([CH2:27][C:28]([NH2:29])=[O:30])[CH2:23][CH2:22][C:21]=3[S:20]4)[CH2:12][CH2:13]2)[CH2:3]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 86695193HCID 86695193, compound

Product 1

HCID 86695194HCID 86695194, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[(3R)-12-[[4-(3-oxopiperazin-1-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetonitrile (330 mg, 0.80 mmol, 1.00 equiv) in methanol (10 mL) was added LiOH.H2O (101 mg, 2.40 mmol, 3.00 equiv) and H2O2 (30%, 0.5 mL) at 0° C. The resulting solution was stirred for 2 h at room temperature and quenched with Na2SO3 (aq.), extracted with DCM (80 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (10:1) to give 50 mg (15%) of 2-[(3R)-12-[[4-(3-oxopiperazin-1-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetamide as a white solid. [Note: The product was found to decompose during column purification].

Workup

  1. customquenched with Na2SO3 (aq.)
  2. extractionextracted with DCM (80 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-783ea4a65b334d198c6ea89a1508edbb
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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