Dichloromethane → 6-Cyano-2,4-dimethyl-11-ethyl-11H-dipyrido[3,2-b:2',3'-e][1,4]diazepine

HRID 1078541

反応式

HRID 1078541 の反応式
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:16][C:17]1[CH:18]=[C:19]([CH3:35])[C:20]2[NH:21][C:22](=O)[C:23]3[CH:33]=[CH:32][CH:31]=[N:30][C:24]=3[N:25]([CH2:28][CH3:29])[C:26]=2[N:27]=1.C(Cl)Cl.[CH:39]([N:42](C(C)C)CC)(C)C>[C-]#N.C([N+](CC)(CC)CC)C.C(OCC)(=O)C>[C:39]([C:22]1[C:23]2[CH:33]=[CH:32][CH:31]=[N:30][C:24]=2[N:25]([CH2:28][CH3:29])[C:26]2[N:27]=[C:17]([CH3:16])[CH:18]=[C:19]([CH3:35])[C:20]=2[N:21]=1)#[N:42]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 463543Dipyridodiazepinone deriv. 5

生成物 1

HCID 194276726-Cyano-2,4-dimethyl-11-ethyl-11H-dipyrido[3,2-b:2',3'-e][1,4]diazepine

試薬・触媒・溶媒 2

HCID 3014735Tetraethylammonium cyanide触媒HCID 8857Ethyl Acetate溶媒

実験手順

Trifluorornethanesulfonic anhydride (0.24 mL, 14 mmol) was added to a solution of 0.314 g (1.2 mmol) 5,11-dihydro-2,4-dimethyl-11-ethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine-6-one in 15 mL of methylene chloride containing 0.25 mL (14 mmol) of diisopropylethylamine. The resulting mixture was refluxed under Ar for 3 hr. Ethyl acetate (~200 mL) was then added and the solution was washed three times with water and four times with brine. After drying (magnesium sulfate), the solution was concentrated in vacuo and the residue dried under high vacuum for 2 hr. The residue was dissolved in 20 mL of methylene chloride, and 0.23 g (14 mol) of tetraethylammonium cyanide was added. After stirring the resulting solution overnight at room temperature, the reaction mixture was concentrated in vacuo. The residue was dissolved in 100 mL of ethyl acetate, and the solution washed with water and brine, and then dried (magnesium sulfate). The solution was concentrated in vacuo and the residue was chromatographed over silica (eluted with 5% ethyl acetate/hexane). The resulting solid was crystallized from heptane to provide 33 mg of the title compound as red crystals, m.p. 154°-155° C.

後処理

  1. temperatureThe resulting mixture was refluxed under Ar for 3 hr
  2. washthe solution was washed three times with water and four times with brine
  3. dry with materialAfter drying (magnesium sulfate)
  4. concentrationthe solution was concentrated in vacuo
  5. customthe residue dried under high vacuum for 2 hr
  6. dissolutionThe residue was dissolved in 20 mL of methylene chloride
  7. concentrationthe reaction mixture was concentrated in vacuo
  8. dissolutionThe residue was dissolved in 100 mL of ethyl acetate
  9. washthe solution washed with water and brine
  10. dry with materialdried (magnesium sulfate)
  11. concentrationThe solution was concentrated in vacuo
  12. customthe residue was chromatographed over silica (eluted with 5% ethyl acetate/hexane)
  13. customThe resulting solid was crystallized from heptane

出典と根拠

ORDレコード
ord-f186d8506f734239944b0dc1b10a8755
出典データセット
uspto-grants-1996_08
特許番号
US05550117

関連ノート

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