4-[1-(2-Carbamoylphenylcarbamoyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester → 4-[1-(4-Oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 238237Notes

Reaction equation

HRID 238237 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16](=O)[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24](=[O:26])[NH2:25])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[Na]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]2[NH:25][C:24](=[O:26])[C:19]3[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:17]=2)[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 599933244-[1-(2-Carbamoylphenylcarbamoyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl esterHCID 178418582HCID 178418582, compound

Product 1

HCID 1361115114-[1-(4-Oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl esterYield 5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[1-(2-carbamoyl-phenylcarbamoyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (20 g, 0.05 mmol, crude from the last step) and MeONa (10 g, 0.19 mol) in MeOH (500 mL) was heated to reflux for 6 hr and the solvent was removed in vacuo. The residue was diluted with water and extracted with EtOAc (300 mL×3), the organic layer was dried with Na2SO4, concentrated and purified by column chromatography to afford the product (2 g, 5%).

Workup

  1. temperatureto reflux for 6 hr
  2. customthe solvent was removed in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc (300 mL×3)
  5. dry with materialthe organic layer was dried with Na2SO4
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-7e1d6d8076e343e881b81f801cb65135
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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