1,4-Dioxane → HCID 59456910, compound

HRID 1362107Notes

Reaction equation

HRID 1362107 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9]CCN(C)C)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:15]([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)(N1C=CN=C1)=[O:16].O1CCOC[CH2:28]1>>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[NH:8][C:15](=[O:16])[N:22]([CH2:26][CH2:25][N:24]([CH3:23])[CH3:28])[CH2:9][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 312751,4-Dioxane2×HCID 682631,1'-Carbonyldiimidazole2×HCID 66967440HCID 66967440, compound

Product 1

HCID 59456910HCID 59456910, compoundYield 50%

Procedure

A solution of 5-bromo-3-[(2-dimethylamino-ethyl)methyl]pyridin-2-ylamine (490 mg, 1.79 mmol) and 1,1′-carbonyldiimidazole (349 mg, 2.15 mmol) in 1,4-dioxane (15 mL) was heated to 80° C. for 14 h. TLC analysis indicated remaining starting material. After cooling, additional 1,1′-carbonyldiimidazole (349 mg, 2.15 mmol) and 1,4-dioxane (10 mL) were added, and the solution was heated to reflux overnight. The solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (80 mL). The solution was washed with satd NaHCO3, water and brine, dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, CH2Cl2/MeOH/Et3N, 92:7:1) gave the title compound (270 mg, 50%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) 69.83 (s, 1H), 8.16 (d, J=2.1 Hz, 1H), 7.76 (s, 1H), 4.48 (s, 2H), 3.37 (t, J=6.5 Hz, 2H), 2.40 (t, J=6.5 Hz, 2H), 2.16 (s, 6H).

Workup

  1. temperatureAfter cooling
  2. temperaturethe solution was heated
  3. temperatureto reflux overnight
  4. customThe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in CH2Cl2 (80 mL)
  6. washThe solution was washed with satd NaHCO3, water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customPurification by column chromatography (silica gel, CH2Cl2/MeOH/Et3N, 92:7:1)

Sources & evidence

ORD record
ord-1ae33547494d4d8b82c85c582b8fe404
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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