Potassium Carbonate → HCID 73504292, compound

HRID 1478572Notes

Reaction equation

HRID 1478572 reaction equation
Cl.[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]3[N:14]([CH2:17][C@H:18]4[O: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.C(=O)([O-])[O-].[K+].[K+].Br[CH:43]([OH:45])[CH3:44]>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][C@@H:18]4[CH2:19][N:20]([C:24]5[N:29]=[CH:28][C:27]([C:30]6[CH2:31][CH2:32][N:33]([CH2:44][CH2:43][OH:45])[CH2:34][CH:35]=6)=[CH:26][N:25]=5)[CH2:21][CH2:22][O:23]4)[N:15]=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[N:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14202443Ethanol, 1-bromo-HCID 118364768HCID 118364768, compound

Product 1

HCID 73504292HCID 73504292, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-2-yl)morpholine HCl salt 330 mg (0.67 mmol) was dissolved in DMF 10 ml, and potassium carbonate 276 mg (1.99 mmol), bromo ethanol 71 μl (0.99 mmol), and TEA 1 ml were added, followed by stirring at room temperature overnight. When the reaction was completed, the reaction mixture was extracted several times with ethyl acetate and brine, and the organic layer was dried over Na2SO4. 7% MeOH/MC chromatography gave a product 210 mg (62%).

Workup

  1. extractionthe reaction mixture was extracted several times with ethyl acetate and brine
  2. dry with materialthe organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-21cb785e9c0440b480075a277121188b
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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