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molecular formula C13H13N3 B1221332 Varenicline CAS No. 249296-44-4

Varenicline

Cat. No. B1221332
M. Wt: 211.26 g/mol
InChI Key: JQSHBVHOMNKWFT-DTORHVGOSA-N
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Patent
US07265119B2

Procedure details

One optimized procedure for making the anhydrous Form B comprises charging a speck-free vessel with between 1.1 and 2.2 equivalents of L-tartaric add and methanol (4 to 50 volumes), and stirring this mixture until dissolved and speck-free filtering the resulting solution into a crystallization vessel. 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene free base (1.0 equivalents) and methanol (4 to 50 volumes) are stirred in a vessel until dissolved at 0 to 50° C., more preferably at 20 to 25° C. The resulting solution of 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene free base is then added over about a period of time ranging from 1 minute to 2 hours, more preferably over about 30 minutes, to the L-tartaric acid solution. The product was allowed to stir at 0 to 40° C., more preferably at 20 to 25° C., for between 1 and 48 hours, more preferably for about 1 hour, and then isolated by filtration. The product is dried generally under vacuum at 20 to 60° C., more preferably at 35 to 45° C., to give Form B of the L-tartrate salt of 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene.
Name
5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Name
5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four
Name
L-tartrate
Name
5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene

Identifiers

REACTION_CXSMILES
[CH:1]12[CH2:16][CH:12]([CH2:13][NH:14][CH2:15]1)[C:11]1[CH:10]=[C:9]3[C:4]([N:5]=[CH:6][CH:7]=[N:8]3)=[CH:3][C:2]2=1.[C:17]([OH:26])(=[O:25])[C@@H:18]([C@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19]>CO>[C:22]([C@@H:20]([C@H:18]([C:17]([O-:26])=[O:25])[OH:19])[OH:21])([O-:24])=[O:23].[CH:12]12[CH2:16][CH:1]([CH2:15][NH:14][CH2:13]1)[C:2]1[CH:3]=[C:4]3[C:9]([N:8]=[CH:7][CH:6]=[N:5]3)=[CH:10][C:11]2=1

Inputs

Step One
Name
5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene
Quantity
0 (± 1) mol
Type
reactant
Smiles
C12C=3C=C4N=CC=NC4=CC3C(CNC1)C2
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene
Quantity
0 (± 1) mol
Type
reactant
Smiles
C12C=3C=C4N=CC=NC4=CC3C(CNC1)C2
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C([C@H](O)[C@@H](O)C(=O)O)(=O)O
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
22.5 (± 2.5) °C
Stirring
Type
CUSTOM
Details
to stir at 0 to 40° C., more preferably at 20 to 25° C., for between 1 and 48 hours, more preferably for about 1 hour
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
of L-tartaric add
DISSOLUTION
Type
DISSOLUTION
Details
until dissolved
DISSOLUTION
Type
DISSOLUTION
Details
until dissolved at 0 to 50° C., more preferably at 20 to 25° C
CUSTOM
Type
CUSTOM
Details
isolated by filtration
CUSTOM
Type
CUSTOM
Details
The product is dried generally under vacuum at 20 to 60° C., more preferably at 35 to 45° C.

Outcomes

Product
Details
Reaction Time
1 h
Name
L-tartrate
Type
product
Smiles
C(=O)([O-])[C@H](O)[C@@H](O)C(=O)[O-]
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.
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