Synthesis routes of Anastrozole EP Impurity I

Anastrozole EP Impurity I

カタログ番号 B193210

: 120511-91-3

分子量: 260.76 g/mol

InChIキー: HSNGPKBBTHINTG-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

USRE036617

Procedure details

A solution of 2,2'-(5-chloromethyl-1,3-phenylene)di(2-methylpropiononitrile), (0.23 g), and 1H-1,2,4-triazole (0.35 g) in acetonitrile (2 ml) was heated under reflux for 18 h, then evaporated to dryness. The residue was partitioned between 1N aqueous potassium hydrogen carbonate solution and ethyl acetate, the organic phase was separated, dried and evaporated to dryness under reduced pressure, and the residue was purified by flash column chromatography. Elution with methanol:chloroform (1:49 by volume), gave 2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methylpropiononitrile), identical with the product of Example 1, and further elution with methanol:chloroform (2:23 by volume, gave 2,2'-[5-(4H-1,2,4-triazol-4-ylmethyl)-1,3-phenylene]di(2-methylpropiononit rile), mp. 158°-161°.

Name

2,2'-(5-chloromethyl-1,3-phenylene)di(2-methylpropiononitrile)

Quantity

0.23 g

Type

reactant

Reaction Step One

Name

1H-1,2,4-triazole

Quantity

0.35 g

Type

reactant

Reaction Step One

Name

acetonitrile

Quantity

2 mL

Type

solvent

Reaction Step One

Name

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methylpropiononitrile)

Identifiers

REACTION_CXSMILES

Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:6]=[C:7]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:8]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1>C(#N)C>[N:19]1([CH2:2][C:3]2[CH:4]=[C:5]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:6]=[C:7]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:8]=2)[CH:23]=[N:22][CH:21]=[N:20]1

Inputs

Step One

Name	2,2'-(5-chloromethyl-1,3-phenylene)di(2-methylpropiononitrile)
Quantity	0.23 g
Type	reactant
Smiles	ClCC=1C=C(C=C(C1)C(C#N)(C)C)C(C#N)(C)C

Name	1H-1,2,4-triazole
Quantity	0.35 g
Type	reactant
Smiles	N1N=CN=C1

Name	acetonitrile
Quantity	2 mL
Type	solvent
Smiles	C(C)#N

Conditions

Other

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

Workups

TEMPERATURE

Type	TEMPERATURE
Details	under reflux for 18 h
Duration	18 h

CUSTOM

Type	CUSTOM
Details	evaporated to dryness

CUSTOM

Type	CUSTOM
Details	The residue was partitioned between 1N aqueous potassium hydrogen carbonate solution and ethyl acetate

CUSTOM

Type	CUSTOM
Details	the organic phase was separated

CUSTOM

Type	CUSTOM
Details	dried

CUSTOM

Type	CUSTOM
Details	evaporated to dryness under reduced pressure

CUSTOM

Type	CUSTOM
Details	the residue was purified by flash column chromatography

WASH

Type	WASH
Details	Elution with methanol:chloroform (1:49 by volume)

Outcomes

Product

Name	2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methylpropiononitrile)
Type	product
Smiles	N1(N=CN=C1)CC=1C=C(C=C(C1)C(C#N)(C)C)C(C#N)(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.