Diethyl Malonate → HCID 135528464, compound

HRID 412301Notes

Reaction equation

HRID 412301 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[N:3]=1.[C:30](OCC)(=[O:37])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].N1CCCCC1>C(O)C>[C:19]([O:18][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][CH:10]([C:6]2[CH:5]=[C:4]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[OH:29])[N:3]=[C:2]3[C:7]=2[CH:8]=[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:30](=[O:37])[NH:1]3)[CH2:11]1)=[O:17])([CH3:21])([CH3:22])[CH3:20]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 136050723HCID 136050723, compound

Product 1

HCID 135528464HCID 135528464, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of tert-butyl 3-[2-amino-3-formyl-6-(2-hydroxyphenyl)4-pyridinyl]-1-piperidinecarboxylate (0.86 g, 2.16 mmol) in ethanol (25 mL) were added diethyl malonate (6.93 g, 43.27 mmol) and piperidine (2.14 mL, 21.64 mmol) and, and the mixture was heated at reflux overnight. The mixture was allowed to cool to room temperature, and then diluted with ethanol. The resulting precipitate was collected by filtration, washed with ethanol and dried under reduced pressure to give ethyl 5-[1-(tert-butoxycarbonyl)-3-piperidinyl]-7-(2-hydroxyphenyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate as a yellow solid (0.752 g, yield; 71%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with ethanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-58f5ddc3d6e8415d8bbf29ff57bfe3de
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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