Trifluoroacetic acid → HCID 118117179, compound

HRID 1774651Notes

Reaction equation

HRID 1774651 reaction equation
[C:1]([NH:5][CH2:6][CH2:7][N:8]([CH3:23])[C:9]1[N:14]=[C:13]([NH:15]C(=O)OC(C)(C)C)[CH:12]=[CH:11][CH:10]=1)(=[O:4])[CH:2]=[CH2:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][C:13]1[N:14]=[C:9]([N:8]([CH3:23])[CH2:7][CH2:6][NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118116622HCID 118116622, compound

Product 1

HCID 118117179HCID 118117179, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 110d (2.0 g, 6.25 mmol) and TFA (2.0 mL) in DCM (10.0 mL) was stirred at rt overnight. The mixture was concentrated and diluted with EA (30 mL), neutralized with 1M NaOH. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by prep-TLC (PE/EA=1/1) to give N-(2-((6-aminopyridin-2-yl)(methyl)amino)ethyl)acrylamide 110e (550 mg, 40%) as yellow oil. ESI-LCMS: m/z=221.2

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EA (30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by prep-TLC (PE/EA=1/1)

Sources & evidence

ORD record
ord-c5652566072b454db14ab2e9ef371126
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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