Hydrochloric Acid → (S)-ethyl 6-bromo-1-(1-(tert-butoxycarbonyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047157Notes

Reaction equation

HRID 1047157 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](F)=[C:6]([CH:19]=1)[C:7]([C:9](=[CH:15][N:16]([CH3:18])C)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8].N[C@H:22]1[CH2:27]C[CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[Br:1][C:2]1[CH:19]=[C:6]2[C:5](=[N:4][CH:3]=1)[N:16]([C@H:18]1[CH2:27][CH2:22][CH2:23][N:24]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:25]1)[CH:15]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:7]2=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylateHCID 68749333Ethyl 2-(5-bromo-2-fluoronicotinoyl)-3-(dimethylamino)acrylate2×

Product 1

HCID 68796045(S)-ethyl 6-bromo-1-(1-(tert-butoxycarbonyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 2-(5-bromo-2-fluoronicotinoyl)-3-(dimethylamino)acrylate (Intermediate 3, 2.0 g, 5.79 mmol), (S)-tert-butyl 3-aminopiperidine-1-carboxylate (1.160 g, 5.79 mmol), and potassium carbonate (2.042 g, 7.38 mmol) were combined in DMF (10.0 mL). The reaction mixture was heated at 90° C. for 2 h. The reaction mixture was cooled to 0° C. and 1N HCl was slowly added until pH was 5. The resulting precipitate was collected by filtration, washed with water and dried overnight to yield a light yellow solid (2.10 g, 75%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried overnight

Sources & evidence

ORD record
ord-a2847f7ada994500b35207c8fa8ab258
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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