Water → HCID 18548980, compound

HRID 276867Notes

Reaction equation

HRID 276867 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1.[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][O-:32].[Na+].O>O1CCCC1>[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][O:32][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 185489566-Fluoro-4-(4-phenoxyanilino)-1,7-naphthyridine-3-carbonitrileHCID 23680072HCID 23680072, compound

Product 1

HCID 18548980HCID 18548980, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 250 mg of 6-fluoro-4-(4-phenoxy-phenylamino)-[1.7]naphthyridine-3-carbonitrile under an inert atmosphere was added 8 mL of 1 M sodium (2-dimethylamino-ethoxide) in tetrahydrofuran. 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 266 mg (85%) of 6-(2-dimethylamino-ethoxy)-4-(4-phenoxy-phenylamino)-[1.7]naphthyridine-3-carbonitrile as a yellow solid: melting point 159-161° C.; mass spectrum (m/e): M+H 426.0

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-483a4cc898c74d71b84720edea26184e
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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