Triethylamine → HCID 118364822, compound

HRID 1478557Notes

Reaction equation

HRID 1478557 reaction equation
[NH2:1][CH2:2][C@H:3]1[O: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][C@H:3]2[O: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 1515269(R)-2-Aminomethyl-4-Boc-morpholine

Product 1

HCID 118364822HCID 118364822, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

(R)-tert-butyl 2-(aminomethyl)morpholine-4-carboxylate (26 g, 124.83 mmol) was dissolved in DMSO (300 ml), and 3,5-dibromopyrazine-2-amine (37.8 g, 149.79 mmol) and Et3N (20.9 ml, 149.79 mmol) were added, followed by stirring at 150° C. for 9 hours. 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 (R)-tert-butyl 2-(((3-amino-6-bromopyrazine-2-yl)amino)methyl)morpholine-4-carboxylate (33.9 g, 70%).

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-2c8c0581b75141aab2091055b8002827
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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