Trifluoroacetic acid → 1-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoxaline-6-carbonitrile

HRID 255362Notes

Reaction equation

HRID 255362 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]1)[C:8](=[O:29])[CH:7]=[N:6]2)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[NH2:21][CH:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][N:9]2[C:10]3[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:12][CH:11]=3)[N:6]=[CH:7][C:8]2=[O:29])[CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86642658tert-butyl{1-[2-(6-cyano-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate2×

Product 1

HCID 667741351-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoxaline-6-carbonitrileYield 87.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {1-[2-(6-cyano-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 198, 0.38 g) in methylene chloride (4 mL) was added at 0° C. TFA (2 mL). After 1 hour, the reaction was diluted with chloroform, washed with saturated solution of Na2CO3, dried (Na2SO4), filtered and concentrated yielding 0.25 g of crude product.

Workup

  1. washwashed with saturated solution of Na2CO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-756c2f311bbb45e0aeabdd44c226bd8b
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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