Triethylamine → HCID 21912943, compound

HRID 1008055Notes

Reaction equation

HRID 1008055 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13](Cl)[C:12]([CH3:19])=[C:11]([CH3:20])[N:10]=1.[S:21]1[CH:25]=[CH:24][N:23]=[C:22]1[CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][NH2:32]>CN(C=O)C>[Cl:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([NH:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][CH2:26][C:22]2[S:21][CH:25]=[CH:24][N:23]=2)[C:12]([CH3:19])=[C:11]([CH3:20])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridineHCID 21913404HCID 21913404, compound

Product 1

HCID 21912943HCID 21912943, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere, triethylamine (3.4 mL, 24 mmol) was added dropwise to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (4.50 g, 20.4 mmol) in anhydrous DMF (45 mL). 2-[3-(1,3-Thiazol-2-yl)propoxy]ethylamine (4.55 g, 24.4 mmol) was then added, and the addition funnel was rinsed with additional DMF (15 mL). The reaction was heated at 60° C. for 3.5 hours. The volatiles were then removed under reduced pressure, and the residue was partitioned between water (100 mL) and diethyl ether (250 mL). The organic layer was washed with water (2×50 mL) and brine (3×50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide an orange oil. The crude product (7.41 g) was purified by column chromatography on silica gel (375 g, eluting with 50:50 hexane:ethyl acetate) to provide a solid, which was dried overnight under high vacuum at room temperature to provide 4.6 g of (2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)-{2-[3-(1,3-thiazol-2-yl)propoxy]ethyl}amine as a yellow solid.

Workup

  1. washthe addition funnel was rinsed with additional DMF (15 mL)
  2. customThe volatiles were then removed under reduced pressure
  3. customthe residue was partitioned between water (100 mL) and diethyl ether (250 mL)
  4. washThe organic layer was washed with water (2×50 mL) and brine (3×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto provide an orange oil
  9. customThe crude product (7.41 g) was purified by column chromatography on silica gel (375 g, eluting with 50:50 hexane:ethyl acetate)
  10. customto provide a solid, which
  11. customwas dried overnight under high vacuum at room temperature

Sources & evidence

ORD record
ord-64447fe79eaf484aaa9ebe120120f00f
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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