Triethylamine → tert-Butyl 3-((3-amino-6-bromopyrazin-2-ylamino)methyl)piperidine-1-carboxylate

HRID 1478591Notes

Reaction equation

HRID 1478591 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.Br[C:17]1[C:18]([NH2:24])=[N:19][CH:20]=[C:21]([Br:23])[N:22]=1.CCN(CC)CC>CS(C)=O>[NH2:24][C:18]1[C:17]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]2)=[N:22][C:21]([Br:23])=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 27564831-Boc-3-(aminomethyl)piperidine

Product 1

HCID 86626415tert-Butyl 3-((3-amino-6-bromopyrazin-2-ylamino)methyl)piperidine-1-carboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

tert-butyl 3-(aminomethyl)piperidine-1-carboxylate (4.97 g, 22.40 mmol) was dissolved in DMSO (80 ml), and then 3,5-dibromopyrazine-2-amine (8.5 g, 33.60 mmol) and Et3N (6.3 ml) were added, followed by stirring at 130° C. overnight. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:1), to give tert-butyl 3-(((3-amino-6-bromopyrazine-2-yl)amino)methyl)piperidine-1-carboxylate (2.19 g, two steps: 26%).

Workup

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with H2O, EA, and brine
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (EA:Hex=1:1)

Sources & evidence

ORD record
ord-f3d96c62a7fc4619acc31183a04d7349
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

Loading…