2-Chloro-5-hydrazinylpyridine → (1aR,5aR)-2-(5-Fluoropyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid Ethyl Ester

HRID 1623919Notes

Reaction equation

HRID 1623919 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5](=[C:7]1[CH2:12][C@@H:11]2[C@@H:9]([CH2:10]2)[C:8]1=O)[O-])[CH3:2].[K+].[F:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][NH2:24])=[N:21][CH:22]=1.ClC1C=CC(NN)=CN=1>>[CH2:1]([O:3][C:4]([C:5]1[C:7]2[CH2:12][C@H:11]3[CH2:10][C@H:9]3[C:8]=2[N:23]([C:20]2[CH:19]=[CH:18][C:17]([F:16])=[CH:22][N:21]=2)[N:24]=1)=[O:14])[CH3:2]

Participants

4

Reactant 3

HCID 108555842-Chloro-5-hydrazinylpyridineHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 68182523potassium 2-ethoxy-2-oxo-((1R,5R)-2-oxobicyclo[3.1.0]hexan-3-ylidene)ethanolate

Product 1

HCID 68182484(1aR,5aR)-2-(5-Fluoropyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid Ethyl Ester

Procedure

The title compound was prepared in a manner similar to that described in Method C using potassium 2-ethoxy-2-oxo-((1R,5R)-2-oxobicyclo[3.1.0]hexan-3-ylidene)ethanolate and mixture of 5-fluoro-2-hydrazinylpyridine and 2-chloro-5-hydrazinylpyridine. LCMS m/z=288.2 [M+H]+.

Sources & evidence

ORD record
ord-3673af21a0bd4ee79dc31e42e3d3a1ae
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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