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

HRID 1665792

Reaction equation

HRID 1665792 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:12]12[CH2:27][CH:23]([CH2:24][NH:25][CH2:26]1)[C:22]1[CH:21]=[C:20]3[C:15]([N:16]=[CH:17][CH:18]=[N:19]3)=[CH:14][C:13]2=1.N>O>[CH:23]12[CH2:27][CH:12]([CH2:26][NH:25][CH2:24]1)[C:13]1[CH:14]=[C:15]3[C:20]([N:19]=[CH:18][CH:17]=[N:16]3)=[CH:21][C:22]2=1

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

In a 250 ml 4 neck round bottom flask equipped with mechanical stirrer, Thermo pocket were charged DM water (30 ml) and 5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene Tosylate salt (10 g, having a total purity of 99.42% obtained in example 4). The above suspension was stirred for 30 minutes at 25-30° C. To this was added 25% aqueous ammonia solution (5 ml) to adjust the pH to 9.0-10 at 25-30° C., and MDC (30 ml) was added to this solution. The resulting mixture was stirred for 30 minutes at 20-25° C. The organic layer was separated, and the aqueous layer was extracted with MDC (4×30 ml). The combined organic layer was washed with DM water (30 ml). The organic layer was treated with activated carbon (1.0 g), and stirred for 30 minutes at 25-30° C. The resulting solution filtered through celite. Concentration afforded a solid product, i.e. 5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene. (Yield-5 g (95.06% (relative to VRN-Tosylate)), HPLC purity-99.43%).

Workup

  1. customobtained in example 4)
  2. customat 25-30° C.
  3. additionMDC (30 ml) was added to this solution
  4. stirringThe resulting mixture was stirred for 30 minutes at 20-25° C
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with MDC (4×30 ml)
  7. washThe combined organic layer was washed with DM water (30 ml)
  8. additionThe organic layer was treated with activated carbon (1.0 g)
  9. stirringstirred for 30 minutes at 25-30° C
  10. filtrationThe resulting solution filtered through celite
  11. concentrationConcentration

Sources & evidence

ORD record
ord-cddf5066e0844a01a2198b36c685bcad
Source dataset
uspto-grants-2011_10
Patent number
US08039620B2

Linked notes

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