Trifluoroacetic acid → HCID 59590052, compound

HRID 1054381Notes

Reaction equation

HRID 1054381 reaction equation
COC1C=CC([O:7][C:8]2[CH:9]=[C:10]([C:14]3[N:19]4[N:20]=[C:21]([NH:23][C:24]5[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]6[CH2:37][CH2:36][CH2:35][CH2:34]6)=[CH:26][CH:25]=5)[N:22]=[C:18]4[CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:12][CH:13]=2)=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[N:33]1([CH2:32][CH2:31][O:30][C:27]2[CH:28]=[CH:29][C:24]([NH:23][C:21]3[N:22]=[C:18]4[CH:17]=[CH:16][CH:15]=[C:14]([C:10]5[CH:9]=[C:8]([OH:7])[CH:13]=[CH:12][CH:11]=5)[N:19]4[N:20]=3)=[CH:25][CH:26]=2)[CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68706245HCID 68706245, compound

Product 1

HCID 59590052HCID 59590052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{5-[3-(4-Methoxy-phenoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (2.90 g, 5.41 mmol) was dissolved in dichloromethane (10 ml). Trifluoroacetic acid (10 ml) was added and the reaction mixture stirred for 2 hours. Neutralisation was performed by adding saturated aqueous sodium hydrogencarbonate. The aqueous was extracted twice with dichloromethane, then the combined organics were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the desired compound. Yield 2.01 g, 89%. 50 mg was purified by preparatory HPLC.

Workup

  1. extractionThe aqueous was extracted twice with dichloromethane
  2. washthe combined organics were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19f9bf9c2f024ee8b34c20447bdc0472
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

Loading…