Triethylamine → HCID 118364791, compound

HRID 1478597Notes

Reaction equation

HRID 1478597 reaction equation
Cl.[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]3[N:14]([CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][N:20]([C:24]5[N:29]=[CH:28][C:27]([C:30]6[CH2:31][CH2:32][NH:33][CH2:34][CH:35]=6)=[CH:26][N:25]=5)[CH2:19]4)[N:15]=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[N:4]1.Br[CH2:37][CH2:38][OH:39].C([O-])([O-])=O.[K+].[K+].CCN(CC)CC>CN(C=O)C>[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]3[N:14]([CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][N:20]([C:24]5[N:29]=[CH:28][C:27]([C:30]6[CH2:31][CH2:32][N:33]([CH2:37][CH2:38][OH:39])[CH2:34][CH:35]=6)=[CH:26][N:25]=5)[CH2:19]4)[N:15]=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[N:4]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 118364779HCID 118364779, compound

Product 1

HCID 118364791HCID 118364791, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(1-methyl-1H-pyrazol-4-yl)-1-((1-(5-(1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)piperidin-3-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine hydrochloride (71 mg, 0.14 mmol) was dissolved in DMF (2 ml), and then 2-bromoethanol (16 μl, 0.22 mmol), K2CO3 (100 mg, 0.72 mmol), and Et3N (100 ul, 0.72 mmol) were added, followed by stirring at room temperature 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 (MeOH:MC=1:10), to give 2-(4-(2-(3-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)piperidin-1-yl)pyrimidin-5-yl)-5,6-dihydropyridin-1(2H)-yl)ethanol (10 mg, 13%).

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 (MeOH:MC=1:10)

Sources & evidence

ORD record
ord-93c24fc52ef5432ab55bebf5a1560723
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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