Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate → (1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)quinoxaline

HRID 1193057Notes

Reaction equation

HRID 1193057 reaction equation
[CH:1]12[N:8]([C:9]3[CH:18]=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)[CH2:7][CH:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.C(OC(N1CCC2C(NC2)C1)=O)(C)(C)C>>[C@@H:1]12[N:8]([C:9]3[CH:18]=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)[CH2:7][C@@H:6]1[CH2:5][CH2:4][NH:3][CH2:2]2

Participants

3

Reactant 2

HCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylateHCID 671166512-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline

Product 1

HCID 68156918(1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)quinoxaline

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 in Step A. MS (ESI) mass calcd. for C14H16N4, 240.3; m/z found, 241.2 [M+H]+. 1H NMR (CDCl3): 8.15 (s, 1H), 7.86 (dd, J=8.4, 1.0, 1H), 7.67 (dd, J=8.4, 1.0, 1H), 7.57-7.34 (m, 1H), 7.40-7.34 (m, 1H), 4.45-4.37 (m, 1H), 4.17-4.10 (m, 1H), 3.86 (dd, J=7.5, 3.4, 1H), 3.57 (dd, J=14.3, 2.0, 1H), 3.10-3.05 (m, 2H), 2.98 (s, 1H), 2.81-2.62 (m, 2H), 2.14-2.03 (m, 1H), 1.84-1.73 (m, 1H).

Sources & evidence

ORD record
ord-51b035812b9245bba5c6bd0061217b95
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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