Trifluoroacetic acid → 5-(Cyclopropylamino)-7-(4-dimethylamino-3-methylphenyl)-[1,6]naphthyridine

HRID 1911086Notes

Reaction equation

HRID 1911086 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[C:14]([CH3:21])[CH:13]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.C(#N)C.O.FC(F)(F)C(O)=O>CN(C)C=O>[CH:22]1([NH:25][C:2]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[C:14]([CH3:21])[CH:13]=3)[CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 69828CyclopropylamineHCID 18373917Acetonitrile--water (1/1)HCID 446328825-Chloro-7-(4-dimethylamino-3-methylphenyl)-[1,6]naphthyridine

Product 1

HCID 584831125-(Cyclopropylamino)-7-(4-dimethylamino-3-methylphenyl)-[1,6]naphthyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

100 mg (0.34 mmol) 6.1, 75 μL (1.07 mmol) cyclopropylamine were dissolved in 500 μl dimethylformamide and stirred overnight at 100° C. The mixture was combined with acetonitrile/water and trifluoroacetic acid and purified by chromatography (RP-HPLC). The corresponding fractions were freeze-dried.

Workup

  1. custompurified by chromatography (RP-HPLC)
  2. customThe corresponding fractions were freeze-dried

Sources & evidence

ORD record
ord-e42da55763a4447a8dcd53ba80037348
Source dataset
uspto-grants-2013_12
Patent number
US08604049B2

Reaction notes

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