Potassium Carbonate → (S)-ethyl 7-(2-(dimethylamino)ethylamino)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047162Notes

Reaction equation

HRID 1047162 reaction equation
F[C:2]1[N:25]=[C:24](F)[C:23]([I:27])=[CH:22][C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH2:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[CH2:20][CH3:21])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH2:38]>CN(C=O)C>[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH:38][C:24]1[N:25]=[C:2]2[C:3]([C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][N:13]2[CH2:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][N:16]2[CH2:20][CH3:21])=[CH:22][C:23]=1[I:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 178472022HCID 178472022, compound2×

Product 1

HCID 69621290(S)-ethyl 7-(2-(dimethylamino)ethylamino)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

(S)-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-((1-ethylpyrrolidin-2-yl)methylamino)acrylate (Intermediate 38, 0.360 g, 0.73 mmol) was taken up in DMF (5 mL), K2CO3 (0.303 g, 2.19 mmol) was added and reaction mixture was heated to 90° C. for 15 min. The reaction mixture cooled to room temperature and N1,N1-dimethylethane-1,2-diamine (0.080 mL, 0.73 mmol) was added and stirred for 15 min. The reaction mixture was quenched with water and extracted with EtOAc 3 times. The combined organics were washed with brine two times, dried over Mg2SO4, and the solvent removed. Crude product was carried on without purification.

Workup

  1. customreaction mixture
  2. temperatureThe reaction mixture cooled to room temperature
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with EtOAc 3 times
  5. washThe combined organics were washed with brine two times
  6. dry with materialdried over Mg2SO4
  7. customthe solvent removed
  8. customCrude product was carried on without purification

Sources & evidence

ORD record
ord-f9f5a7622b774e2ca3df8d10fc3e83a3
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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