Ethyl Acetate → HCID 58816573, compound

HRID 2354080Notes

Reaction equation

HRID 2354080 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14](=O)[CH2:15][NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1.CO>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=2)=[O:18])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 68690135HCID 68690135, compound

Product 1

HCID 58816573HCID 58816573, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The crude 1-[2-(4-benzyl-piperidin-1-yl)-2-oxo-ethyl]-3-(2-methyl-pyridin-4-yl)-urea (Example 39.1., 0.5 mmol) is dissolved in THF (5 mL) and added to a cooled (0° C.) suspension of LiAlH4 (100 mg, 2.5 mmol) in THF (20 mL). The mixture is warmed during 15 h to r.t. The reaction mixture is carefully added to EtOAc (100 mL) and MeOH (5 mL), and, subsequently, sat. aq. NaHCO3 (2 mL) are added. The mixture is filtered, the filtercake washed with MeOH (2×50 mL), and the filtrate is evaporated. The residue is taken up in a minimal amount of MeOH, diluted with CH2Cl2, dried (Na2SO4), filtered and evaporated. The residue is purified by HPLC to provide the title compound.

Workup

  1. additionadded to
  2. temperaturea cooled
  3. temperatureThe mixture is warmed during 15 h to r.t
  4. filtrationThe mixture is filtered
  5. washthe filtercake washed with MeOH (2×50 mL)
  6. customthe filtrate is evaporated
  7. additiondiluted with CH2Cl2
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-2794d66e7f904de4bf8478c953bf4f27
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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