Potassium Hydroxide → HCID 86681850, compound

HRID 406215Notes

Reaction equation

HRID 406215 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC>[C:1]1([C:7]2[N:8]=[C:9]3[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 79177tert-Butyl bromoacetate2×HCID 66666416HCID 66666416, compound

Product 1

HCID 86681850HCID 86681850, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst2×HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 4-(2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butan-1-ol (step 3) (50 mg, 0.139 mmol) in toluene (1 ml) was added KOH (40% aq, 1 ml, 0.139 mmol) and tetrabutylammonium hydrogen sulfate (47.2 mg, 0.139 mmol) followed after 5 min at RT, by tertiary butyl bromoacetate (90 uL). The reaction mixture was stirred at RT for 24 h. The mixture was diluted with ether and the phases were separated. The aqueous portion was extracted with ether (×2), the combined organics were dried (sodium sulphate), filtered and the solvent removed in vacuo. The residue was dissolved in THF (1 ml) followed by the addition of KOH (40% aq, 1 ml, 0.139 mmol), tetrabutylammonium hydrogen sulfate (47.2 mg, 0.139 mmol) and tertiary butyl bromoacetate (88 uL). The reaction mixture was stirred at RT for 6 h. The mixture was diluted with ether and stirred at RT for 12 h. The phases were separated, the aqueous extracted with ether (×2), the combined organics were dried (sodium sulphate), filtered and the solvent removed in vacuo. The crude material was purified on silica eluting with 0-100% EtOAc/DCM to afford the title compound:

Workup

  1. customthe phases were separated
  2. extractionThe aqueous portion was extracted with ether (×2)
  3. dry with materialthe combined organics were dried (sodium sulphate)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue was dissolved in THF (1 ml)
  7. stirringThe reaction mixture was stirred at RT for 6 h
  8. stirringstirred at RT for 12 h
  9. customThe phases were separated
  10. extractionthe aqueous extracted with ether (×2)
  11. dry with materialthe combined organics were dried (sodium sulphate)
  12. filtrationfiltered
  13. customthe solvent removed in vacuo
  14. customThe crude material was purified on silica eluting with 0-100% EtOAc/DCM

Sources & evidence

ORD record
ord-e7507a4b4ff0429b840849f6ec7a806f
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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