Acetone → HCID 57665028, compound

HRID 1717248Notes

Reaction equation

HRID 1717248 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=2)[N:8]=[N:7][C:6]=1[C:22]([NH:24][CH:25]1[CH2:27][CH2:26]1)=[O:23])CC=C.C(#N)C.O.C[N+]1([O-])CC[O:36]CC1.[CH3:40][C:41]([CH3:43])=[O:42]>[Os](=O)(=O)(=O)=O>[CH:25]1([NH:24][C:22]([C:6]2[N:7]=[N:8][N:9]([C:10]3[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=3)[C:5]=2[CH2:1][CH2:40][CH:41]([OH:42])[CH2:43][OH:36])=[O:23])[CH2:27][CH2:26]1

Participants

7

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 6342AcetonitrileHCID 82029Methyl morpholine oxideHCID 57665100HCID 57665100, compound

Product 1

HCID 57665028HCID 57665028, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 5-(3-buten-1-yl)-N-cyclopropyl-1-(4-{[(ethylamino)carbonyl]amino}phenyl)-1H-1,2,3-triazole-4-carboxamide obtained in Example 41 in acetone (3 ml)-acetonitrile (3 ml)—water (3 ml) were added N-methylmorpholine N-oxide (0.18 g) and microencapsulated osmium tetroxide (containing 10%, 0.5 g). The reaction mixture was stirred at room temperature for 4 days, and the insoluble material was filtered off. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (ethyl acetate/methanol=9/1 to ethyl acetate/methanol=7/3). The resultant product was recrystallized from ethyl acetate/hexane to give the title compound as colorless crystals (0.12 g, 23%).

Workup

  1. filtrationthe insoluble material was filtered off
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column (ethyl acetate/methanol=9/1 to ethyl acetate/methanol=7/3)
  4. customThe resultant product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-288f163b8a3d4ade8e2bb6f2d87565e4
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…