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

HRID 982326노트

반응식

HRID 982326 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8d7cbc06f6074220a7514988c4bd0fc1
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04996205

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