Trifluoroacetic acid → HCID 118116346, compound

HRID 1774662Notes

Reaction equation

HRID 1774662 reaction equation
[C:1]([NH:5][C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[N:17]=[C:16]([NH:18]C(=O)OC(C)(C)C)[CH:15]=[CH:14][CH:13]=2)[CH2:7]1)(=[O:4])[CH:2]=[CH2:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:18][C:16]1[N:17]=[C:12]([N:8]2[CH2:9][CH2:10][CH2:11][C@H:6]([NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[CH2:7]2)[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118116322HCID 118116322, compound

Product 1

HCID 118116346HCID 118116346, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 114d (880 mg, 2.53 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 (S)—N-(1-(6-aminopyridin-2-yl)piperidin-3-yl)acrylamide 114e (440 mg, 70%) as yellow oil. MS-ESI: [M+H]+ 247.2

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-fbceaf7336b245389aec263d18fc875c
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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