Triethylamine → HCID 117966410, compound

HRID 931275Notes

Reaction equation

HRID 931275 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]([CH:5]1[CH:10]([CH3:11])[CH2:9][CH2:8][NH:7][CH2:6]1)=[O:4].C(N(CC)CC)C.Cl[C:21]1[N:26]=[C:25]([NH2:27])[C:24]([N+:28]([O-:30])=[O:29])=[CH:23][CH:22]=1>CS(C)=O.O>[NH2:27][C:25]1[N:26]=[C:21]([N:7]2[CH2:8][CH2:9][C@H:10]([CH3:11])[C@H:5]([C:3]([N:2]([CH3:12])[CH3:1])=[O:4])[CH2:6]2)[CH:22]=[CH:23][C:24]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 89854330HCID 89854330, compound

Product 1

HCID 117966410HCID 117966410, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N,N,4-trimethylpiperidine-3-carboxamide (0.16 g, 0.96 mmol) in dimethylsulfoxide (5 mL) were added triethylamine (0.2 mL, 0.96 mmol) and 6-chloro-3-nitropyridin-2-amine (0.168 g, 0.96 mmol). The reaction mixture was heated for 12 h at 80° C., then was cooled. The mixture was diluted with water and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via silica gel chromatography to afford cis-1-(6-amino-5-nitropyridin-2-yl)-N,N,4-trimethylpiperidine-3-carboxamide (0.2 g, 68%).

Workup

  1. temperaturewas cooled
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-68b50260ba8e41b18a1f47c992a775ed
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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