Synthesis routes of Sumatriptan

Sumatriptan

カタログ番号 B127528

: 103628-46-2

分子量: 295.40 g/mol

InChIキー: KQKPFRSPSRPDEB-UHFFFAOYSA-N

注意: 研究専用です。人間または獣医用ではありません。

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Patent

US06255502B1

Procedure details

Sumatriptan caprate and hydroxypropyl-beta cyclodextrin (HPB) were complexed by the kneading method. Sumatriptan caprate (1.254 g) and HPB (3.748 g) were blended together. Water (4.5 mL) was added and the mixture ground together in a mortar with a pestle to form a uniform paste. Grinding was continued for 30 minutes. The paste was then dried in a vacuum oven (40° C.; 0 bar) for 48 hours. The solid mass was broken up, passed through a 60 mesh screen and returned to the vacuum oven (40° C.; 0 bar) for 12 hours in order to ensure uniform drying of the complex. Analysis by HPLC for sumatriptan base content, and Karl Fischer for moisture content gave the following results: % sumatriptan base was 16.40% and the moisture content was 3.45%. The complex was characterised by DSC, FT-IR and XRD.

Name

Sumatriptan caprate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

hydroxypropyl-beta cyclodextrin

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

Sumatriptan caprate

Quantity

1.254 g

Type

reactant

Reaction Step Three

Name

HPB

Quantity

3.748 g

Type

reactant

Reaction Step Four

Name

Water

Quantity

4.5 mL

Type

solvent

Reaction Step Five

Name

sumatriptan

Identifiers

REACTION_CXSMILES

[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4].[O-]C(CCCCCCCCC)=O.CC(O)COC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8COCC(O)C)O[C@@H]7COCC(O)C)O[C@@H]6COCC(O)C)O[C@@H]5COCC(O)C)O[C@@H]4COCC(O)C)O[C@@H]3COCC(O)C>O>[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4] |f:0.1|

Inputs

Step One

Name	Sumatriptan caprate
Quantity	0 (± 1) mol
Type	reactant
Smiles	CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C.[O-]C(=O)CCCCCCCCC

Step Two

Name	hydroxypropyl-beta cyclodextrin
Quantity	0 (± 1) mol
Type	reactant
Smiles	CC(COC[C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@@H]([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@H](O2)[C@@H]([C@H]8O)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)O)O)O

Step Three

Name	Sumatriptan caprate
Quantity	1.254 g
Type	reactant
Smiles	CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C.[O-]C(=O)CCCCCCCCC

Step Four

Name	HPB
Quantity	3.748 g
Type	reactant
Smiles	CC(COC[C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@@H]([C@@H]([C@H]7O)O)O[C@@H]8[C@H](O[C@H](O2)[C@@H]([C@H]8O)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)COCC(C)O)O)O)O

Step Five

Name	Water
Quantity	4.5 mL
Type	solvent
Smiles	O

Conditions

Other

Conditions are dynamic	1
Details	See reaction.notes.procedure_details.

Workups

CUSTOM

Type	CUSTOM
Details	the mixture ground together in a mortar with a pestle to form a uniform paste

CUSTOM

Type	CUSTOM
Details	Grinding

CUSTOM

Type	CUSTOM
Details	The paste was then dried in a vacuum oven (40° C.; 0 bar) for 48 hours
Duration	48 h

WAIT

Type	WAIT
Details	returned to the vacuum oven (40° C.; 0 bar) for 12 hours in order
Duration	12 h

CUSTOM

Type	CUSTOM
Details	to ensure uniform drying of the complex

Outcomes

Product

Details

Reaction Time

30 min

Name	sumatriptan
Type	product
Smiles	CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C

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.