Ethyl Acetate → HCID 59715933, compound

HRID 2223727Notes

Reaction equation

HRID 2223727 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[CH:9]=[C:10]([CH:36]=[CH:37][CH:38]=1)[CH:11]=[C:12]1[CH2:17][CH2:16][N:15]([C:18](=O)[CH2:19][NH:20][C:21]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[C:26]([CH3:34])[CH:25]=2)=[O:22])[CH2:14][CH2:13]1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1.CO>[CH3:7][C:8]1[CH:9]=[C:10]([CH:36]=[CH:37][CH:38]=1)[CH:11]=[C:12]1[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][NH:20][C:21]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[C:26]([CH3:34])[CH:25]=2)=[O:22])[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 59715927HCID 59715927, compound

Product 1

HCID 59715933HCID 59715933, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (100 mg, 2.6 mmol) in THF (40 mL) is added a solution of crude 1-{2-[4-(3-methyl-benzylidene)-piperidin-1-yl]-2-oxo-ethyl}3-(2-methyl-quinolin-4-yl)-urea (1 mmol) in THF (10 mL) and the mixture is stirred at room temperature for 15 h. The suspension is poured slowly into EtOAc (200 mL) and MeOH (10 mL) and, subsequently, sat. NaHCO3 (dropwise, total of 1.5 mL) is added. The precipitate is filtered off and washed with MeOH (2×20 mL). The filtrate is dried (Na2SO4), filtered and evaporated. The residue is purified by flash chromatography (SiO2, CH2Cl2-MeOH, 10:1) to provide the title compound.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with MeOH (2×20 mL)
  3. dry with materialThe filtrate is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by flash chromatography (SiO2, CH2Cl2-MeOH, 10:1)

Sources & evidence

ORD record
ord-31e5069fa0a44e47ae548b221d08efc1
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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