Triethylamine → HCID 89853938, compound

HRID 931119Notes

Reaction equation

HRID 931119 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[O:12][CH2:11][CH2:10][NH:9][CH2:8]1.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>[N+:28]([C:24]1[C:25]([NH2:27])=[N:26][C:21]([N:9]2[CH2:10][CH2:11][O:12][CH:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:8]2)=[CH:22][CH:23]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 193534032-(Pyridin-2-yl)morpholine

Product 1

HCID 89853938HCID 89853938, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(pyridin-2-yl)morpholine (0.1 g, 0.609 mmol) in dimethylsulfoxide (5 mL) was added triethylamine (0.17 mL, 1.2 mmol). The resulting solution was stirred for 10 min at room temperature, and then 6-chloro-3-nitropyridin-2-amine (105 mg, 0.609 mmol) was added. The reaction mixture was heated at 110° C. for 4 h, and then was cooled to room temperature. Ice water was added and the mixture was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via flash chromatography (80% ethyl acetate in petroleum ether) to afford the title compound (0.1 g, 55%). MS (ES+) (M+H) 302.25.

Workup

  1. temperatureThe reaction mixture was heated at 110° C. for 4 h
  2. temperaturewas cooled to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via flash chromatography (80% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-7138bd8821064d2e9b9b7e5993620d61
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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