Trifluoroacetic acid → HCID 66848221, compound

HRID 536596Notes

Reaction equation

HRID 536596 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH:10]2[N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17][C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:11]2)=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:13]1[C:12]2([CH2:17][CH2:18][NH:19][CH:10]([CH2:9][NH:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)[CH2:11]2)[CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66848050HCID 66848050, compound2×

Product 1

HCID 66848221HCID 66848221, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(±)tert-butyl 7-(((5-chloropyridin-2-yl)amino)methyl)-8-azaspiro[4.5]decane-8-carboxylate (intermediate 74, 1 g, 2.63 mmol) was dissolved in dichloromethane (10 ml) and cooled to 0° C., then trifluoroacetic acid (30 ml) was added. After 1 hour at 0° C. and 2 hours at room temperature the solution was evaporated, the residue re-dissolved in dichloromethane was washed with saturated NaHCO3 aqueous solution. The organic layers were dried (Na2SO4) and concentrated under vacuum to obtain Obtained 600 mg of the title compound.

Workup

  1. custom2 hours at room temperature the solution was evaporated
  2. dissolutionthe residue re-dissolved in dichloromethane
  3. washwas washed with saturated NaHCO3 aqueous solution
  4. dry with materialThe organic layers were dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customto obtain

Sources & evidence

ORD record
ord-0368f8c85106447dbaaac6c2a5972be9
Source dataset
uspto-grants-2014_10
Patent number
US08859608B2

Reaction notes

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