Trifluoroacetic acid → HCID 72710846, compound

HRID 921832Notes

Reaction equation

HRID 921832 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][OH:11])[C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]([CH:31]2[CH2:33][CH2:32]2)CC2C=CC(OC)=CC=2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>ClCCCl>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][OH:11])[C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([NH:21][CH:31]2[CH2:33][CH2:32]2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 89922864HCID 89922864, compound

Product 1

HCID 72710846HCID 72710846, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-((2-chloro-5-cyano-4-(3-hydroxypropyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (30 mg, 0.057 mmol) was taken up in DCE (0.6 mL) and anisole (0.031 mL, 0.284 mmol) was added, followed by TFA (0.175 mli, 2.268 mmol). The reaction was stirred at room temperature overnight. LCMS indicates formation of the TFA ester. The solvent was removed in vacuo and the material dissolved in 2N NH3 in MeOH. The solution was stirred at room temperature for 30 min. The solvent was removed in vacuo and the material was triturated with Et2O to remove the anisole. The material was purified by preparative HPLC to provide 2-((2-chloro-5-cyano-4-(3-hydroxypropyl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (6.2 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe material dissolved in 2N NH3 in MeOH
  3. stirringThe solution was stirred at room temperature for 30 min
  4. customThe solvent was removed in vacuo
  5. customthe material was triturated with Et2O
  6. customto remove the anisole
  7. customThe material was purified by preparative HPLC

Sources & evidence

ORD record
ord-b49a6054ceb24159816cfa7b174d0a66
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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