3-Chloro-2,5-dimethylpyrazine → (1R,6S)-8-(3,6-Dimethyl-pyrazin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

HRID 1193062Notes

Reaction equation

HRID 1193062 reaction equation
[CH:1]12[N:8]([C:9]3[CH:18]=[N:17][C:16]4[C:11](=[CH:12]C=CC=4)[N:10]=3)[CH2:7][CH:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.[C:19](OC(N1CCC2C(NC2)C1)=O)(C)(C)C.ClC1C(C)=NC=C(C)N=1.ClC1C=NC2C(=CC=CC=2)N=1>>[CH3:19][C:18]1[C:9]([N:8]2[C@@H:1]3[C@@H:6]([CH2:5][CH2:4][NH:3][CH2:2]3)[CH2:7]2)=[N:10][C:11]([CH3:12])=[CH:16][N:17]=1

Participants

5

Reactant 4

HCID 667713-Chloro-2,5-dimethylpyrazineHCID 2389382-ChloroquinoxalineHCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate2×HCID 671166512-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline

Product 1

HCID 68157557(1R,6S)-8-(3,6-Dimethyl-pyrazin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Procedure

The title compound was prepared in a manner analogous to Intermediate 2, substituting (1R,6S)-(3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester for 3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester and 3-chloro-2,5-dimethyl-pyrazine for 2-chloro-quinoxaline in Step A. MS (ESI) mass calcd. for C12H18N4, 218.30. The compound was used as such in the subsequent reactions.

Sources & evidence

ORD record
ord-6f88fd13f75648bfbc14abc6abe29524
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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