Water → Ethyl 6-(1-(tert-butoxycarbonyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylate

HRID 531146Notes

Reaction equation

HRID 531146 reaction equation
[CH2:1]([C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]([C:15]([O:17]CC)=O)=[C:6]([CH:20]=[CH2:21])[N:5]=1)[CH2:2][CH3:3].[NH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1.C(N(C(C)C)C(C)C)C.O>CC(N(C)C)=O>[C:32]([O:31][C:29]([N:26]1[CH2:27][CH2:28][CH:23]([N:22]2[CH2:21][CH2:20][C:6]3[N:5]=[C:4]([CH2:1][CH2:2][CH3:3])[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=3[C:15]2=[O:17])[CH2:24][CH2:25]1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 117992132Diethyl 2-propyl-6-vinylpyridine-3,5-dicarboxylate

Product 1

HCID 117992199Ethyl 6-(1-(tert-butoxycarbonyl)piperidin-4-yl)-5-oxo-2-propyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carboxylateYield 72.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of diethyl 2-propyl-6-vinylpyridine-3,5-dicarboxylate (9.00 g), tert-butyl 4-aminopiperidine-1-carboxylate (7.42 g) and N-ethyl-N-isopropylpropan-2-amine (8.09 mL) in DMA (45 mL) was stirred at 130 to 140° C. for 4.5 hours. The mixture was poured into water at room temperature and extracted with ethyl acetate. The organic layer was separated, washed with brine twice, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was passed through a silica gel-pad (hexane/ethyl acetate), and concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (10.0 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ceeb86ec95854fa98f44333411389f62
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

Loading…