Water → HCID 66665909, compound

HRID 406200

Reaction equation

HRID 406200 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[C:7]1([CH3:37])[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH:29]=[CH:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:16]3=[N:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[CH:9][CH:8]=1.S(=O)(O)[O-:39].[Na+].[OH2:43]>[Cl-].C([N+](CCCC)(CCCC)C)CCC.C(Cl)Cl>[OH:43][CH:28]1[CH2:27][N:26]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[C:16]2=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:13]([C:10]3[CH:9]=[CH:8][C:7]([CH3:37])=[CH:12][CH:11]=3)[N:14]=[C:15]2[CH:29]1[OH:39]

Participants

7

Reactant 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 66666278HCID 66666278, compound

Product 1

HCID 66665909HCID 66665909, compound

Reagents, catalysts & solvents 2

HCID 91822Tributylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tributylmethylammonium chloride (0.970 g, 4.11 mmol) in DCM (15 ml) at RT under nitrogen was added potassium permanganate (0.650 g, 4.11 mmol) portionwise over 10 minutes. The mixture was cooled to 0° C. and treated dropwise with a solution of tert-butyl 2,3-dip-tolylpyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 2) (1 g, 2.418 mmol) in DCM (10 ml). A solution of sodium bisulfite (1.510 g, 14.51 mmol) in water (12.5 ml) was added keeping the temperature <10° C. The mixture was filtered through Celite® (filter material), washing with DCM. The phases were separated and the organic portion was washed with brine, dried (sodium sulphate), filtered and the solvent was removed in vacuo. The crude product was dissolved in DCM and purified by chromatography on silica eluting with 30-50% EtOAc in iso-hexanes to afford the title compound;

Workup

  1. customthe temperature <10° C
  2. filtrationThe mixture was filtered through Celite® (filter material)
  3. washwashing with DCM
  4. customThe phases were separated
  5. washthe organic portion was washed with brine
  6. dry with materialdried (sodium sulphate)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. dissolutionThe crude product was dissolved in DCM
  10. custompurified by chromatography on silica eluting with 30-50% EtOAc in iso-hexanes

Sources & evidence

ORD record
ord-5e2b1906b94441489d4cd006247cd8ce
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Linked notes

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