Sumatriptan
Número de catálogo B127528
Peso molecular: 295.40 g/mol
Clave InChI: KQKPFRSPSRPDEB-UHFFFAOYSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
Patent
US06281357B1
Procedure details
To a stirred slurry of calcium turnings (243 mg, 6 mmol) in tetrahydrofuran (4 ml) at −40° C. was condensed liquid ammonia (4 ml). The blue bronze was stirred at −50 to −40° C. for a further 15 min, before a solution of 1-[1-benzyl-3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-diphenylmethyl-N-methylmethanesulfonamide (from step (e), 836 mg, 1.5 mmol) in tetrahydrofuran (2 ml) was added dropwise, maintaining the temperature below −40° C. The dark blue solution was stirred at −40° C. for a further 30 minutes, before saturated ammonium chloride solution (10 ml) was added dropwise and the grey solution warmed to ambient temperature. Water (10 ml) was then added and the white slurry stirred for 15 min, before being filtered in vacuo. The solid was then dissolved in 5N HCl (12 ml) and the resulting orange solution extracted with ethyl acetate (10 ml). The pH of the aqueous phase was then adjusted (pH=10) with 10N NaOH which resulted in precipitation. The solid was filtered and dried in vacuo at 50° C. overnight to yield the title compound (250 mg, 56%) as a white solid. m.p. 159-163° C.
Name
calcium
Quantity
243 mg
Type
reactant
Reaction Step One
[Compound]
Name
bronze
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
1-[1-benzyl-3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-diphenylmethyl-N-methylmethanesulfonamide
Quantity
836 mg
Type
reactant
Reaction Step Three
Name
Yield
56%
Identifiers
|
REACTION_CXSMILES
|
[Ca].N.C([N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][S:20]([N:23](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:24])(=[O:22])=[O:21])=[CH:16][CH:17]=2)[C:12]([CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])=[CH:11]1)C1C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1.O>[CH3:42][N:40]([CH3:41])[CH2:39][CH2:38][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([CH2:19][S:20]([NH:23][CH3:24])(=[O:21])=[O:22])[CH:14]=2)[NH:10][CH:11]=1 |f:3.4|
|
Inputs
Step One
|
Name
|
calcium
|
|
Quantity
|
243 mg
|
|
Type
|
reactant
|
|
Smiles
|
[Ca]
|
Step Two
|
Name
|
|
|
Quantity
|
4 mL
|
|
Type
|
reactant
|
|
Smiles
|
N
|
Step Three
[Compound]
|
Name
|
bronze
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
1-[1-benzyl-3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-diphenylmethyl-N-methylmethanesulfonamide
|
|
Quantity
|
836 mg
|
|
Type
|
reactant
|
|
Smiles
|
C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)CS(=O)(=O)N(C)C(C1=CC=CC=C1)C1=CC=CC=C1)CCN(C)C
|
|
Name
|
|
|
Quantity
|
2 mL
|
|
Type
|
solvent
|
|
Smiles
|
O1CCCC1
|
Step Four
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
reactant
|
|
Smiles
|
[Cl-].[NH4+]
|
Step Five
|
Name
|
|
|
Quantity
|
4 mL
|
|
Type
|
solvent
|
|
Smiles
|
O1CCCC1
|
Step Six
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
the white slurry stirred for 15 min
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
at −40° C.
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
was added dropwise
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
maintaining the temperature below −40° C
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
was added dropwise
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
before being filtered in vacuo
|
DISSOLUTION
|
Type
|
DISSOLUTION
|
|
Details
|
The solid was then dissolved in 5N HCl (12 ml)
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the resulting orange solution extracted with ethyl acetate (10 ml)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
resulted in precipitation
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The solid was filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried in vacuo at 50° C. overnight
|
|
Duration
|
8 (± 8) h
|
Outcomes
Product
Details
Reaction Time |
15 min |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CN(CCC1=CNC2=CC=C(C=C12)CS(=O)(=O)NC)C
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 250 mg | |
| YIELD: PERCENTYIELD | 56% | |
| YIELD: CALCULATEDPERCENTYIELD | 56.4% |
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. |
