Synthesis routes of Varenicline

Varenicline

Número de catálogo B1221332

: 249296-44-4

Peso molecular: 211.26 g/mol

Clave InChI: JQSHBVHOMNKWFT-DTORHVGOSA-N

Atención: Solo para uso de investigación. No para uso humano o veterinario.

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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

Quantity

250 mL

Type

reactant

Reaction Step One

Name

ammonia

Quantity

5 mL

Type

reactant

Reaction Step Two

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

water

Quantity

30 mL

Type

solvent

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	ammonia
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	water
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

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.