Trifluoroacetic acid → [5-(3-Aminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

HRID 1971578Notes

Reaction equation

HRID 1971578 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:20]3[N:21]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)=[CH:27][CH:26]=4)[N:23]=[C:19]3[CH:18]=[CH:17][CH:16]=2)[CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]3[N:21]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]5[CH2:35][CH2:36][CH2:37][CH2:38]5)=[CH:27][CH:26]=4)[N:23]=[C:19]3[CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59590092(3-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 59589633[5-(3-Aminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-benzyl)-carbamic acid tert-butyl ester (1.78 g, 3.37 mmol) was dissolved in dichloromethane (20 ml). Trifluoroacetic acid (20 ml) was added and the reaction was stirred for 2 hours. Neutralisation was performed by adding saturated aqueous sodium hydrogencarbonate. The aqueous phase was extracted twice with dichloromethane, and the combined organics washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the desired compound. Yield: 460 mg, 32%. 50 mg was purified by preparatory HPLC.

Workup

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

Sources & evidence

ORD record
ord-39dabdcf1324405bb0fd09ae141c3a86
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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