Trifluoroacetic acid → 7-(Piperidin-1-yl)-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

HRID 517907Notes

Reaction equation

HRID 517907 reaction equation
[N:1]1([CH:7]2[CH2:30][N:29](C(OC(C)(C)C)=O)[C:10]3=[N:11][C:12]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)[N:14]=[C:9]3[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1([CH:7]2[CH2:30][NH:29][C:10]3=[N:11][C:12]([C:22]4[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=4)=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)[N:14]=[C:9]3[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89690064tert-Butyl 7-(piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Product 1

HCID 896900517-(Piperidin-1-yl)-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 7-(piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 6) (90 mg, 0.180 mmol) in DCM (1 ml) was treated with TFA (0.501 mL, 6.50 mmol) and stirred at room temperature for 3 hours. The resulting mixture was diluted with DCM (3 ml) and washed with a saturated solution of sodium hydrogen carbonate. The organic portion was passed through a phase separating column and the solvent removed under reduced pressure to afford the titled compound;

Workup

  1. washwashed with a saturated solution of sodium hydrogen carbonate
  2. customseparating column
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-745070d4da5440068ce355b34ae9c643
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

Loading…