Diisopropylethylamine → HCID 118114056, compound

HRID 706456Notes

Reaction equation

HRID 706456 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-fe11a67b33e0449c9c1a42a8c7d091c0
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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