Trifluoroacetic acid → HCID 89919657, compound

HRID 921802Notes

Reaction equation

HRID 921802 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][C:11]2[N:16]=[C:15]([N:17]([CH:27]3[CH2:29][CH2:28]3)CC3C=CC(OC)=CC=3)[C:14]3=[N:30][CH:31]=[C:32]([C:33]#[N:34])[N:13]3[N:12]=2)=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>ClCCCl>[Cl:1][C:2]1[C:3]([NH:10][C:11]2[N:16]=[C:15]([NH:17][CH:27]3[CH2:28][CH2:29]3)[C:14]3=[N:30][CH:31]=[C:32]([C:33]#[N:34])[N:13]3[N:12]=2)=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 89919584HCID 89919584, compound

Product 1

HCID 89919657HCID 89919657, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

2-((5-Chloro-2-cyanopyrimidin-4-yl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile was dissolved in DCE. Anisole (50 μL) was added followed by TFA (200 μL) and the reaction was stirred at 50° C. overnight. The reaction was concentrated and dried under vacuum. The crude product was purified by preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19×250 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 0-100% B over 15 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions concentrated and dried via centrifugal evaporation to afford 3.6 mg of 2-((5-Chloro-2-cyanopyrimidin-4-yl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile.

Workup

  1. concentrationThe reaction was concentrated
  2. customdried under vacuum
  3. customThe crude product was purified by preparative LC/MS with the following conditions
  4. waitGradient: 0-100% B over 15 minutes
  5. customa 5-minute hold
  6. concentrationFractions concentrated
  7. customdried via centrifugal evaporation

Sources & evidence

ORD record
ord-2de1288c257742e2ae915be1e1cf8749
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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