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

HRID 1266285Notes

Reaction equation

HRID 1266285 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]([NH:19]CC4C=CC(OC)=CC=4)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:29]#[N:30])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[NH2:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][N:15]=1)[N:12]=[CH:11][C:10]([C:29]#[N:30])=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 129691054-(3-Bromo-phenylamino)-6-(4-methoxy-benzylamino)-[1,7]naphthyridine-3-carbonitrile

Product 1

HCID 97980066-Amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrileYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 400 mg of 4-(3-bromo-phenylamino)-6-(4-methoxy-benzylamino)-[1,7]naphthyridine-3-carbonitrile in 10 mL of methylene chloride was added 10 mL of trifluoroacetic acid. After stirring under an inert atmosphere for 20 hours, 10 mL of toluene was added and the solvents were stripped on a rotary evaporator. The product was purified by flash chromatography with a gradient of 0-5% methanol/chloroform to give 250 mg of 6-amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile as an off-white solid: melting point 185-190° C. (decomposed); mass spectrum (m/e): M+H 340.0, 342.1.

Workup

  1. customthe solvents were stripped on a rotary evaporator
  2. customThe product was purified by flash chromatography with a gradient of 0-5% methanol/chloroform

Sources & evidence

ORD record
ord-b112f7fdb3244175b4bd717f07911945
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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