2,6-Dimethoxybenzoyl chloride → (2,6-Dimethoxy-phenyl)-(8-quinoxalin-2-yl-3,8-diaza-bicyclo[4.2.0]oct-3-yl)-methanone

HRID 1193132Notes

Reaction equation

HRID 1193132 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@@H]12N(C3C=NC4C(=CC=CC=4)N=3)C[C@@H]1CCNC2.[CH3:37][O:38][C:39]1[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH3:49])[C:40]=1[C:41](Cl)=[O:42].C1(C2C=CC=CC=2)C(C(Cl)=O)=CC=CC=1>>[CH3:49][O:48][C:44]1[CH:45]=[CH:46][CH:47]=[C:39]([O:38][CH3:37])[C:40]=1[C:41]([N:3]1[CH2:4][CH2:5][CH:6]2[CH:1]([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]2)[CH2:2]1)=[O:42]

Participants

5

Reactant 4

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 671166512-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline2×HCID 68156918(1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)quinoxaline

Product 1

HCID 67117118(2,6-Dimethoxy-phenyl)-(8-quinoxalin-2-yl-3,8-diaza-bicyclo[4.2.0]oct-3-yl)-methanone

Procedure

The title compound was prepared in a manner analogous to Example 5, substituting the trifluoro acetic acid salt of 2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline (Intermediate 2) for (1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline and 2,6-dimethoxy benzoyl chloride for biphenyl-2-carbonyl chloride. MS (ESI) mass calcd. for C23H24N4O3, 404.46; m/z found, 405.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.25 (s, 0.25H), 7.98 (s, 0.75H), 7.90-7.80 (m, 1H), 7.60-7.47 (m, 1H), 7.44-7.30 (m, 2H), 7.23 (t, J=8.4, 0.25H), 7.13 (t, J=8.4, 0.75H), 6.58-6.44 (m, 1.25H), 6.03 (d, J=8.4, 0.75H), 4.90-4.56 (m, 1H), 4.32-3.84 (m, 3H), 3.81 (s, 6H), 3.78-3.56 (m, 1H), 3.50-3.30 (m, 1H), 3.17-2.91 (m, 1H), 2.41-1.53 (m, 3H).

Sources & evidence

ORD record
ord-a34de3f4a4324a0b8241d662518166bc
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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