Trifluoroacetic acid → HCID 59589844, compound

HRID 1472838Notes

Reaction equation

HRID 1472838 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[N:19]3[N:20]=[C:21]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:26][CH:25]=4)[N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)[CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[NH2:7][C:8]1[CH:9]=[C:10]([C:14]2[N:19]3[N:20]=[C:21]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]5[CH2:34][CH2:35][CH2:36][CH2:37]5)=[CH:26][CH:25]=4)[N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68703789HCID 68703789, compound

Product 1

HCID 59589844HCID 59589844, compound

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}-phenyl)-carbamic acid tert-butyl ester (1.39 g, 2.71 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 phase was extracted twice with dichloromethane, and the combined organics washed with brine, dried over anhydrous magnesium sulgate, filtered and concentrated in vacuo to give the desired compound. Yield 830 mg, 74%. 50 mg was purified by preparatory LCMS.

Workup

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

Sources & evidence

ORD record
ord-355b463b444041fca34c7339fdd7144b
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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