2-Oxopropiononitrile → HCID 86680477, compound

HRID 1777420Notes

Reaction equation

HRID 1777420 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2OC(=O)[S:10][N:9]=2)=[CH:4][CH:3]=1.[C:14]([C:17]#[N:18])(=[O:16])[CH3:15]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:18]=[C:17]([C:14](=[O:16])[CH3:15])[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 694302-OxopropiononitrileHCID 14087130HCID 14087130, compound

Product 1

HCID 86680477HCID 86680477, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In still a further embodiment, 1-(3-(4-fluorophenyl)-1,2,4-thiadiazol-5-yl)ethanone may be prepared according to the methodology and reagents of Scheme 16A. In this embodiment, a 1,3,4-oxathiazol-2-one ring fragment is generated and subsequently converted to a 1,2,4-thiadiazole ring fragment during the preparation of 1-(3-(4-fluorophenyl)-1,2,4-thiadiazol-5-yl)ethanone. Specifically, 4-fluorobenzamide is reacted with chlorocarbonylsulfenyl chloride to provide 5-(4-fluoro-phenyl)-1,3,4-oxathiazol-2-one. In one embodiment, the reaction is performed in toluene. In another embodiment, the reaction is performed at elevated temperatures of about 80° C. for about 3 hours. 5-(4-Fluorophenyl)-1,3,4-oxathiazol-2-one is then reacted with acetyl cyanide to provide 1-(3-(4-fluorophenyl)-1,2,4-thiadiazol-5-yl)-ethanone. In one embodiment, this reaction is performed in 1,2-dichlorobenzene. In another embodiment, this reaction is performed at elevated temperatures of about 160° C. for about 20 hours. 1-(3-(4-Fluorophenyl)-1,2,4-thiadiazol-5-yl)ethanone is then converted to a compound of Formula (I-A) by the methods described herein, such as Scheme 1.

Sources & evidence

ORD record
ord-578ccc0fa34645848d90e8f7e8e65d31
Source dataset
uspto-grants-2016_02
Patent number
US09266873B2

Reaction notes

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