Triethylamine → HCID 89853938, compound

HRID 931108Notes

Reaction equation

HRID 931108 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[O:13][CH2:12][CH2:11][NH:10][CH2:9]1.C(N(CC)CC)C.Cl[C:22]1[N:27]=[C:26]([NH2:28])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][CH:23]=1.C(OCC)(=O)C>CS(C)=O>[N+:29]([C:25]1[C:26]([NH2:28])=[N:27][C:22]([N:10]2[CH2:11][CH2:12][O:13][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=3)[CH2:9]2)=[CH:23][CH:24]=1)([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 70290093HCID 70290093, compound

Product 1

HCID 89853938HCID 89853938, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(pyridin-2-yl)morpholine hydrochloride (1000 mg, 4.22 mmol) and triethylamine (1.3 mL, 9.3 mmol) in dimethylsulfoxide (10 mL) was added 6-chloro-3-nitropyridin-2-amine (734 mg, 4.23 mmol). The reaction mixture was stirred at 100° C. for 18 h. The reaction mixture was cooled to room temperature. Ethyl acetate was added and the mixture was washed with water (20 mL). The aqueous layer was extracted with ethyl acetate (20 mL×2). The combined organics were washed with brine (20 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via flash chromatography (40-100% ethyl acetate in heptanes) to afford the title compound (0.897 g, 70%). 1H NMR (400 MHz, CDCl3) δ 3.08 (s, 1H), 3.18-3.29 (m, 1H), 3.83 (s, 1H), 4.20 (s, 1H), 4.41 (d, 1H), 4.63 (dd, 1H), 4.67-4.80 (m, 1H), 6.18 (s, 1H), 7.23-7.26 (m, 1H), 7.54 (s, 1H), 7.75 (s, 1H), 8.22 (s, 1H), 8.60 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washthe mixture was washed with water (20 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (20 mL×2)
  4. washThe combined organics were washed with brine (20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified via flash chromatography (40-100% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-7ea94f67b7a348b8a3ce1c56959d9714
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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