2-Methoxyethylamine → 5-Chloro-6-[(2-methoxyethyl)amino]nicotinonitrile

HRID 1631008Notes

Reaction equation

HRID 1631008 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[Cl:6][C:7]1[C:8](Cl)=[N:9][CH:10]=[C:11]([CH:14]=1)[C:12]#[N:13]>O1CCOCC1>[Cl:6][C:7]1[C:8]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[N:9][CH:10]=[C:11]([CH:14]=1)[C:12]#[N:13]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 128784645,6-Dichloropyridine-3-carbonitrile

Product 1

HCID 585542235-Chloro-6-[(2-methoxyethyl)amino]nicotinonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-methoxyethyl amine (4.11 mL, 43.9 mmol), TEA (6.11 mL, 43.9 mmol) and 5,6-dichloronicotinonitrile (Bionet GC-0755, 7.6 g, 43.9 mmol) was prepared in dioxane and stirred at RT for 24 hours. The reaction mixture was filtered to remove inorganic solids and filtrate was concentrated under reduced pressure. The residue taken up with EtOAc (100 mL) and washed with water (3×100 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. After purification by flash chromatography (silica, pet ether/EtOAc), the title compound was obtained as a white powder (6.9 g, 75%). LC/MS, M+(ESI): 212.1. 1H NMR (DMSO-d6, 400 MHz) δ 8.42 (1H, d), 8.07 (1H, d), 7.48 (1H, t), 3.58 (2H, m), 3.47 (2H, m), 3.23 (3H, s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove inorganic solids and filtrate
  3. concentrationwas concentrated under reduced pressure
  4. washwashed with water (3×100 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customAfter purification by flash chromatography (silica, pet ether/EtOAc)

Sources & evidence

ORD record
ord-417ddcd8f6e84a2baffa3d5d98a160f8
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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