Trifluoroacetic acid → HCID 89923004, compound

HRID 921896Notes

Reaction equation

HRID 921896 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([CH3:10])=[CH2:9])=[CH:6][C:5]([C:11]#[N:12])=[CH:4][C:3]=1[NH:13][C:14]1[N:19]=[C:18]([N:20]([CH:30]2[CH2:32][CH2:31]2)CC2C=CC(OC)=CC=2)[C:17]2=[N:33][CH:34]=[C:35]([C:36]#[N:37])[N:16]2[N:15]=1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([CH3:10])=[CH2:9])=[CH:6][C:5]([C:11]#[N:12])=[CH:4][C:3]=1[NH:13][C:14]1[N:19]=[C:18]([NH:20][CH:30]2[CH2:32][CH2:31]2)[C:17]2=[N:33][CH:34]=[C:35]([C:36]#[N:37])[N:16]2[N:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 1182534612-((2-Chloro-5-cyano-3-(prop-1-en-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Product 1

HCID 89923004HCID 89923004, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-((2-chloro-5-cyano-3-(prop-1-en-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (748 mg, 1.46 mmol) and anisole (4.00 mL, 36.6 mmol) in DCM (23 mL) and TFA (23 mL, 290 mmol) was left stirring at room temperature overnight. The solvents were removed and the yellow solid was suspended in DCM. This was washed with saturated aq. NaHCO3 solution and dried with sodium sulfate. The solvent was removed and the residue was suspended in a mixture of EtOAc: hexane=1:1. This was filtered to give 2-((2-chloro-5-cyano-3-(prop-1-en-2-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (365 mg) as a light yellow solid.

Workup

  1. customThe solvents were removed
  2. washThis was washed with saturated aq. NaHCO3 solution
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was removed
  5. additionthe residue was suspended in a mixture of EtOAc
  6. filtrationThis was filtered

Sources & evidence

ORD record
ord-977d6786d4de42deb0b2aca24538f80a
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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