Diisopropylethylamine → HCID 118114056, compound

HRID 2178335Notes

Reaction equation

HRID 2178335 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:18][NH2:19])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=1.Cl[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][C:24]([I:30])=[CH:23][N:22]=1.C(N(CC)C(C)C)(C)C>C(#N)C.O>[I:30][C:24]1[CH:25]=[C:26]([N+:27]([O-:29])=[O:28])[C:21]([NH:19][CH2:18][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]3[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:22][CH:23]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 15142942-Chloro-5-iodo-3-nitropyridineHCID 118113974(3-Methoxy-4((6-methylpyridin-3-yl)methoxy)phenyl)methanamine

Product 1

HCID 118114056HCID 118114056, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (3-methoxy-4-((6-methylpyridin-3-yl)methoxy)phenyl)methanamine (7.30 g, 28.26 mmol) in acetonitrile (200 mL) was added 2-chloro-5-iodo-3-nitropyridine (8.44 g, 29.67 mmol) and N,N-diisopropylethylamine (5.48 g, 42.39 mmol). The brown mixture was heated to reflux. After 5 h, the brown mixture was allowed to cool to room temperature and was diluted with water (600 mL). The resulting precipitate was isolated by filtration and washed with water (200 mL). The moist solids were dissolved in ethyl acetate (300 mL), and this solution was washed with water (100 mL). The organic phase was dried over magnesium sulfate, filtered, and concentrated to provide 13.57 g (95%) of 5-iodo-N-(3-methoxy-4-((6-methylpyridin-3-yl)methoxy)benzyl)-3-nitropyridin-2-amine as a bright yellow solid.

Workup

  1. temperatureThe brown mixture was heated to reflux
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water (200 mL)
  4. dissolutionThe moist solids were dissolved in ethyl acetate (300 mL)
  5. washthis solution was washed with water (100 mL)
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3d245ebff2f4438b92797b02ad8afa95
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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