Trifluoroacetic acid → HCID 69182729, compound

HRID 2113572Notes

Reaction equation

HRID 2113572 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[C:17]([NH:20]CC4C=CC(OC)=CC=4)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:30]#[N:31])[CH:5]=[CH:6][C:7]=1[F:8].FC(F)(F)C(O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][N:16]=1)[N:13]=[CH:12][C:11]([C:30]#[N:31])=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69315368HCID 69315368, compound

Product 1

HCID 69182729HCID 69182729, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[(3-chloro-4-fluorophenyl)amino]-6-[(4-methoxybenzyl)amino]-1,7-naphthyridine-3-carbonitrile (0.623 g, 1.45 mmol) and trifluoroacetic acid (14.5 mL) in methylene chloride 14.5 mL was stirred at room temperature overnight. The reaction was diluted with toluene and the solvents were evaporated. The crude product was purified by flash column chromatography (3% MeOH in CHCl3) to give a yellow solid (0.287 g, 64%). 1H NMR (400 MHz, DMSO-D6) 8 ppm 7.1 (s, 1 H) 7.3 (m, 1 H) 7.5 (t, J=9.0 Hz, 1 H) 7.6 (dd, J=6.2, 2.4 Hz, 1 H) 8.4 (s, 1 H) 8.8 (s, 1 H) 10.0 (s, 1 H)

Workup

  1. customthe solvents were evaporated
  2. customThe crude product was purified by flash column chromatography (3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-b9c4df0510d54ab892b71519c48a6e3e
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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