Varenicline
货号 B1221332
分子量: 211.26 g/mol
InChI 键: JQSHBVHOMNKWFT-DTORHVGOSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US08039620B2
Procedure details
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%).
[Compound]
Name
4
Quantity
250 mL
Type
reactant
Reaction Step One
Name
5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene Tosylate salt
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene
Identifiers
|
REACTION_CXSMILES
|
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 |f:0.1|
|
Inputs
Step One
[Compound]
|
Name
|
4
|
|
Quantity
|
250 mL
|
|
Type
|
reactant
|
|
Smiles
|
|
Step Two
|
Name
|
|
|
Quantity
|
5 mL
|
|
Type
|
reactant
|
|
Smiles
|
N
|
Step Three
|
Name
|
5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene Tosylate salt
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
S(=O)(=O)(O)C1=CC=C(C)C=C1.C12C=3C=C4N=CC=NC4=CC3C(CNC1)C2
|
|
Name
|
|
|
Quantity
|
30 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
27.5 (± 2.5) °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
The above suspension was stirred for 30 minutes at 25-30° C
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
obtained in example 4)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
at 25-30° C.
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
MDC (30 ml) was added to this solution
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
The resulting mixture was stirred for 30 minutes at 20-25° C
|
|
Duration
|
30 min
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The organic layer was separated
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the aqueous layer was extracted with MDC (4×30 ml)
|
WASH
|
Type
|
WASH
|
|
Details
|
The combined organic layer was washed with DM water (30 ml)
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
The organic layer was treated with activated carbon (1.0 g)
|
STIRRING
|
Type
|
STIRRING
|
|
Details
|
stirred for 30 minutes at 25-30° C
|
|
Duration
|
30 min
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The resulting solution filtered through celite
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
Concentration
|
Outcomes
Product
Details
Reaction Time |
30 min |
|
Name
|
5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene
|
|
Type
|
product
|
|
Smiles
|
C12C=3C=C4N=CC=NC4=CC3C(CNC1)C2
|
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
