Trifluoroacetic acid → 6-Amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile

HRID 276858Notes

Reaction equation

HRID 276858 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([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])[CH:5]=[CH:6][CH:7]=1.COC1C=CC(C[NH2:29])=CC=1.CO.C(Cl)(Cl)Cl.FC(F)(F)C(O)=O>C(O)C.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[NH2:29][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][N:15]=1)[N:12]=[CH:11][C:10]([C:20]#[N:21])=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 754524-MethoxybenzylamineHCID 185489794-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrileHCID 21584188Chloroform methanol

Product 1

HCID 97980066-Amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

To 1.3 g of 4-(3-bromo-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile in 20 mL of absolute ethanol was added 5 ml of 4-methoxy-benzylamine. The reaction was refluxed for six days, stripped of solvents, and passed through a plug of silica gel with 5% methanol/chloroform. This crude product was dissolved in 10 mL of chloroform containing 5% anisole and 10 mL of trifluoroacetic acid was added. After stirring under an inert atmosphere for 20 hours, 10 mL of toluene was added and the solvents stripped on a rotary evaporator. The product was purified by flash chromatography with a gradient of 0-10% methanol/chloroform. The solid was extracted with hot, 5% methanol/isopropyl ether and then cooled, filtered, and dried to give 250 mg of 6-amino-4-(3-bromo-phenylamino)-[1.7]naphthyridine-3-carbonitrile as an off-white solid. mass spectrum (m/e): M+H 306.2.

Workup

  1. temperatureThe reaction was refluxed for six days
  2. customthe solvents stripped on a rotary evaporator
  3. customThe product was purified by flash chromatography with a gradient of 0-10% methanol/chloroform
  4. extractionThe solid was extracted with hot, 5% methanol/isopropyl ether
  5. temperaturecooled
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-6d2ad1b6640247b58f8e221f0e4a0ebf
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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