Trifluoroacetic acid → HCID 59589844, compound

HRID 1054384Notes

Reaction equation

HRID 1054384 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 sulfate, 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 sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a2947f36d0b4d328415bfce6866f189
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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