Ammonia → 5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene

HRID 1665794

반응식

HRID 1665794 반응식
O.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:13]12[CH2:28][CH:24]([CH2:25][NH:26][CH2:27]1)[C:23]1[CH:22]=[C:21]3[C:16]([N:17]=[CH:18][CH:19]=[N:20]3)=[CH:15][C:14]2=1.N>CCCCCCC>[CH:24]12[CH2:28][CH:13]([CH2:27][NH:26][CH2:25]1)[C:14]1[CH:15]=[C:16]3[C:21]([N:20]=[CH:19][CH:18]=[N:17]3)=[CH:22][C:23]2=1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 962WaterHCID 866377745,8,14-Triazatetracyclo[10.3.1.02, 11.04,9]hexadeca-2(11),3,5,7,9-pentaene tosylate salt

생성물 1

HCID 1703615,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene

시약·촉매·용매 1

HCID 8900Heptane용매

반응 조건

온도
27.5 °C

실험 절차

In a 3.0 lit 4 neck round bottom flask equipped with mechanical stirrer, Thermo pocket were charged DM water (507 ml) and 5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene tosylate salt (169 g having a total purity of 99.99% obtained in example 6). The above suspension was stirred for 30 minutes at 25-30° C. To this was added 25% aqueous ammonia solution (60 ml) to adjust the pH to 9.0-10 at 25-30° C., and maintained with stirring for 30 minutes. MDC (507 ml) was charged in this solution. The resulting mixture was stirred for 30 minutes at 20-25° C. The layers were separated, and the aqueous layer was extracted with MDC (4×507 ml). The combined organic layer washed with DM water (507 ml). The organic layer was treated with activated Carbon (16.9 g), and stirred for 30 minutes at 25-30° C. The resulting solution was filtered through celite, concentrated to leave 1 volume of MDC with product, charged with 845 ml n-heptane at 45-50° C., and distilled under vacuum to remove a mixture of MDC and n-heptane to leave 3 volumes of n-heptane. The solid material was cooled to 25-30° C., and filtered at 25-30° C. to afford a solid product, i.e. 5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene. The solid obtained was dried in vacuum oven at 45° to 50° C. (Yield—84 g (94.49% (relative to VRN-Tosylate)), HPLC purity—99.97%).

후처리

  1. customIn a 3.0 lit 4 neck round bottom flask equipped with mechanical stirrer
  2. customobtained in example 6)
  3. customat 25-30° C.
  4. temperaturemaintained
  5. stirringwith stirring for 30 minutes
  6. additionMDC (507 ml) was charged in this solution
  7. stirringThe resulting mixture was stirred for 30 minutes at 20-25° C
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with MDC (4×507 ml)
  10. washThe combined organic layer washed with DM water (507 ml)
  11. additionThe organic layer was treated with activated Carbon (16.9 g)
  12. stirringstirred for 30 minutes at 25-30° C
  13. filtrationThe resulting solution was filtered through celite
  14. concentrationconcentrated
  15. customto leave 1 volume of MDC with product
  16. distillationdistilled under vacuum
  17. customto remove
  18. additiona mixture of MDC and n-heptane
  19. customto leave 3 volumes of n-heptane
  20. temperatureThe solid material was cooled to 25-30° C.
  21. filtrationfiltered at 25-30° C.

출처 및 근거

ORD 기록
ord-c990c374af634df48cf58984abceaad9
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039620B2

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