6-Fluoro4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrile → HCID 18548946, compound

HRID 1266300Notes

Reaction equation

HRID 1266300 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]([CH3:21])=[C:17]([OH:22])[CH:16]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][O-:27].[Na+]>O1CCCC1.O>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][O:27][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]([CH3:21])=[C:17]([OH:22])[CH:16]=1

Participants

5

Reactant 2

HCID 185489376-Fluoro4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrileHCID 23680072HCID 23680072, compound

Product 1

HCID 18548946HCID 18548946, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 160 mg of 6-fluoro-4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrile under an inert atmosphere was added 3 mL of 1 M sodium (2-dimethylamino-ethoxide) in tetrahydrofuran. After refluxing for 3 hours, the reaction was diluted with Water and the product extracted five times with chloroform. The crude product was purified by flash chromatography with 1% triethyl amine and 10% methanol/chloroform followed by recrystallized from chloroform/ether to give 106 mg of 6-(2-dimethylamino-ethoxy)-4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrile as a yellowish solid: melting point 100-180° C. (decomposed, effervescence); mass spectrum (m/e): M+H 419.9.

Workup

  1. temperatureAfter refluxing for 3 hours
  2. extractionthe product extracted five times with chloroform
  3. customThe crude product was purified by flash chromatography with 1% triethyl amine and 10% methanol/chloroform
  4. customby recrystallized from chloroform/ether

Sources & evidence

ORD record
ord-6050983bbd5b47deb4afe3b106cc7e56
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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