Methyl Isocyanate → 10,11-dihydro-5-methyl-11-methylcarbamyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

HRID 982326ノート

反応式

HRID 982326 の反応式
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:7]=2[NH:6][CH2:5][C:4]2=[CH:13][CH:14]=[CH:15][N:3]12.[CH3:16][N:17]=[C:18]=[O:19]>C1C=CC=CC=1>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:7]=2[N:6]([C:18](=[O:19])[NH:17][CH3:16])[CH2:5][C:4]2=[CH:13][CH:14]=[CH:15][N:3]12

参加物

4

反応物 2

HCID 12228Methyl IsocyanateHCID 1460194810,11-dihydro-5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

生成物 1

HCID 1460195610,11-dihydro-5-methyl-11-methylcarbamyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
70 °C

実験手順

A solution of 3.7 g of 10,11-dihydro-5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine in 100 ml of benzene was treated with 1.6 ml of methyl isocyanate and then stirred at 70° C. for five hours. After cooling, the mixture was evaporated under reduced pressure and the residue was dissolved in water. The aqueous layer extracted with ethyl acetate. The combined organic layer was washed with water followed by a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification of the residue was achieved by means of high pressure liquid chromatography (silica gel; elution with 2.5% methanol/dichloromethane) to afford 2.3 g of 10,11-dihydro-5-methyl-11-methylcarbamyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine m.p. 197°-200° C. (dec.). The solid was dissolved in ethanol and acidified with an ethanol solution of maleic acid to precipitate the corresponding maleate salt. Recrystallization of the salt from ethanol yielded 1.8 g of 10,11-dihydro-5-methyl-11 -methylcarbamyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine maleate, m.p. 160°-161° C.

後処理

  1. temperatureAfter cooling
  2. customthe mixture was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionThe aqueous layer extracted with ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue
  10. washwas achieved by means of high pressure liquid chromatography (silica gel; elution with 2.5% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-8d7cbc06f6074220a7514988c4bd0fc1
出典データセット
uspto-grants-1991_02
特許番号
US04996205

反応ノート

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