Trifluoroacetic acid → 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-cyano-1,5-naphthyridin-2(1H)-one

HRID 656925Notes

Reaction equation

HRID 656925 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:29])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[N:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH3:2].[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:10]2[C:9](=[O:29])[CH:8]=[CH:7][C:6]3[N:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:12][C:11]2=3)[CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71248370tert-butyl (1-(2-(7-cyano-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 2

HCID 222AmmoniaHCID 688165971-(2-(4-aminopiperidin-1-yl)ethyl)-7-cyano-1,5-naphthyridin-2(1H)-oneYield 139.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl {1-[2-(7-cyano-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-piperidinyl}carbamate (0.411 g, 1.03 mmol) in DCM (16 ml) was added TFA (9 ml) and the reaction stirred at rt for 1 h. The solution was evaporated, dissolved in MeOH and passed through a column of Amberlyst A21 basic resin. The fractions containing the desired product were evaporated and the residue was subjected to column chromatography on silica gel using a DCM:MeOH:aq NH3 gradient to provide the desired compound (0.214 g, 70%).

Workup

  1. customThe solution was evaporated
  2. dissolutiondissolved in MeOH
  3. additionThe fractions containing the desired product
  4. customwere evaporated

Sources & evidence

ORD record
ord-4c15af5bd9174126808a128703f5c241
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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