Trifluoroacetic acid → HCID 59590052, compound

HRID 1971569Notes

Reaction equation

HRID 1971569 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-8de5afdfa7414163985aa2883625cdfa
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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