Potassium Carbonate → 2-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-N,N-dimethylacetamide

HRID 711375Notes

Reaction equation

HRID 711375 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[N:13][N:14]([CH:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[C:5]=3[C:4]=2[N:3]=1.Cl[CH2:22][C:23]([N:25]([CH3:27])[CH3:26])=[O:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[N:13][N:14]([CH:15]4[CH2:20][CH2:19][N:18]([CH2:22][C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH2:17][CH2:16]4)[C:5]=3[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 866906968-chloro-1-(piperidin-4-yl)-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridine

Product 1

HCID 866907002-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-N,N-dimethylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-chloro-1-(piperidin-4-yl)-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridine (100 mg, 0.35 mmol), 2-chloro-N,N-dimethylacetamide (46 mg, 0.38 mmol), and K2CO3 (97 mg, 1.04 mmol) in DMF (5 mL) was stirred at r.t. overnight. The solvent was removed, and the residue was extracted with EtOAc (3×10 mL). The combined organic layers were dried over Na2SO4, and concentrated to afford crude 2-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-N,N-dimethylacetamide, which was used in the next step without further purification.

Workup

  1. customThe solvent was removed
  2. extractionthe residue was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e355de8965f04ff5a132271acd4f2a71
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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