Trifluoroacetic acid → HCID 89923297, compound

HRID 921881Notes

Reaction equation

HRID 921881 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]3[CH2:14][CH2:15][N:16]([CH3:19])[C:17](=[O:18])[CH:10]3[CH2:9]2)=[CH:6][C:5]([C:20]#[N:21])=[CH:4][C:3]=1[NH:22]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:22][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([N:8]2[CH2:13][CH2:12][N:11]3[CH2:14][CH2:15][N:16]([CH3:19])[C:17](=[O:18])[CH:10]3[CH2:9]2)[C:2]=1[Cl:1])[C:20]#[N:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734944HCID 131734944, compound

Product 1

HCID 89923297HCID 89923297, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of racemic tert-butyl (2-chloro-5-cyano-3-(8-methyl-9-oxohexahydro-1H-pyrazino[1,2-a]pyrazin-2(6H)-yl)phenyl)carbamate (60 mg, 0.143 mmol) in DCM (1.5 mL) was added 1 mL of TFA. After stirring for 1 h, LC-MS indicated completion. It was concentrated and purification via flash chromatography (0-5% MeOH in DCM, 12 g) gave racemic 3-amino-4-chloro-5-(8-methyl-9-oxohexahydro-1H-pyrazino[1,2-a]pyrazin-2(6H)-yl)benzonitrile (35 mg, 0.109 mmol, 77% yield) as a yellow solid.

Workup

  1. concentrationIt was concentrated
  2. custompurification via flash chromatography (0-5% MeOH in DCM, 12 g)

Sources & evidence

ORD record
ord-141d3e0a2e3d412fa2f59dc6e33b4aab
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

Loading…