Tetrahydrofuran → 4-(4-Chloro-2-fluoro-phenylamino)-6-(2-dimethylamino-ethoxy)-[1,7]naphthyridine-3-carbonitrile

HRID 276870Notes

Reaction equation

HRID 276870 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16](F)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:20]#[N:21])=[C:4]([F:22])[CH:3]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][O-:27].[Na+].O1CCCC1>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([O:27][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:20]#[N:21])=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 185489394-(4-Chloro-2-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrileHCID 23680072Sodium (2dimethylamino-ethoxide)

Product 1

HCID 185489424-(4-Chloro-2-fluoro-phenylamino)-6-(2-dimethylamino-ethoxy)-[1,7]naphthyridine-3-carbonitrileYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 250 mg of 4-(4-chloro-2-fluoro-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile under an inert atmosphere was added 8 mL of 1 M sodium (2-dimethylamino-ethoxide) in tetrahydrofaran. After refluxing for 2 hours, the reaction was stripped of tetrahydrofuran and water was added. The product was filtered, washed with water, dried, and recrystallized from chloroform/ether/hexanes to give 204 mg (64%) of 4-(4-chloro-2-fluoro-phenylamino)-6-(2-dimethylamino-ethoxy)-[1.7]naphthyridine-3-carbonitrile as a yellow solid: melting point 150-152° C.; mass spectrum (m/e): M+H 385.9.

Workup

  1. temperatureAfter refluxing for 2 hours
  2. additionwas added
  3. filtrationThe product was filtered
  4. washwashed with water
  5. customdried
  6. customrecrystallized from chloroform/ether/hexanes

Sources & evidence

ORD record
ord-f485798df0f841a18be592060250c855
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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