molecular formula C14H14ClF5N4O2S B8278460 4-(2-Chloro-2,2-difluoroethyl)-1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one

4-(2-Chloro-2,2-difluoroethyl)-1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one

Cat. No.: B8278460

M. Wt: 432.8 g/mol

InChI Key: DCXFIOLWWRXEQH-UHFFFAOYSA-N

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Overview

1. Description

3. Synthesis routes and methods

2. Properties

4. Disclaimer

Description

4-(2-Chloro-2,2-difluoroethyl)-1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one is a useful research compound. Its molecular formula is C14H14ClF5N4O2S and its molecular weight is 432.8 g/mol. The purity is usually 95%.
BenchChem offers high-quality this compound suitable for many research applications. Different packaging options are available to accommodate customers' requirements. Please inquire for more information about this compound including the price, delivery time, and more detailed information at [email protected].

Properties

Molecular Formula	C14H14ClF5N4O2S
Molecular Weight	432.8 g/mol
IUPAC Name	4-(2-chloro-2,2-difluoroethyl)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one
InChI	InChI=1S/C14H14ClF5N4O2S/c1-26-6-9-22-24-8(11(14(18,19)20)21-12(24)27-9)5-23-4-7(2-10(23)25)3-13(15,16)17/h7H,2-6H2,1H3
InChI Key	DCXFIOLWWRXEQH-UHFFFAOYSA-N
Canonical SMILES	COCC1=NN2C(=C(N=C2S1)C(F)(F)F)CN3CC(CC3=O)CC(F)(F)Cl
Origin of Product	United States

Synthesis routes and methods

Procedure details

To a hot solution (80° C.) of ZnCl2 (0.23 g, 1.69 mmol, 10 mol %) and 2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole a28 (4 g, 16.96 mmol) in dioxane (200 ml) is added a solution of 4-(2-chloro-2,2-difluoroethyl)-1-(chloromethyl)pyrrolidin-2-one a18 in dioxane (5 ml). The reaction mixture is heated at 85° C. for 5 days, then a further 2 g of pyrrolidinone a18 is added in one portion and the reaction mixture is kept under agitation at 90° C. for 1 day. A further addition of pyrrolidinone a18 (2 g) in order to insure complete conversion of compound a28 and further heating of the reaction mixture at reflux for 3 days increased significatively the conversion of imidazo[2,1-b][1,3,4]thiadiazole a28. After cooling and hydrolysis (250 ml of water), the crude mixture is extracted by CH2Cl2 (2×250 ml). The cumulated organic layers are dried over MgSO4, filtered and condensed under reduced pressure. The residue is purified over silicagel (eluent: CH2Cl2/MeOH/NH4OH 99/1/0.1) to afford 4-(2-chloro-2,2-difluoroethyl)-1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one 4.

Name

pyrrolidinone

Quantity

2 g

Type

reactant

Reaction Step One

Name

pyrrolidinone

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

imidazo[2,1-b][1,3,4]thiadiazole

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

4-(2-chloro-2,2-difluoroethyl)-1-(chloromethyl)pyrrolidin-2-one

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

dioxane

Quantity

200 mL

Type

solvent

Reaction Step Four

Name

dioxane

Quantity

5 mL

Type

solvent

Reaction Step Four

Name

ZnCl2

Quantity

0.23 g

Type

catalyst

Reaction Step Four

Name

water

Quantity

250 mL

Type

solvent

Reaction Step Five

Name

4-(2-chloro-2,2-difluoroethyl)-1-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-one

Yield

74%

Details

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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.

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