2-(Pyridin-3-yl)benzoic acid → (1R,6S)(2-Pyridin-3-yl-phenyl)-(8-quinoxalin-2-yl-3,8-diaza-bicyclo[4.2.0]oct-3-yl)-methanone

HRID 1193133Notes

Reaction equation

HRID 1193133 reaction equation
[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.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=2[C:43](O)=[O:44])[CH:36]=1.S1C=CC=C1C1C=CC=CC=1C(O)=O>>[N:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=2[C:43]([N:3]2[CH2:4][CH2:5][C@@H:6]3[C@@H:1]([N:8]([C:9]4[CH:18]=[N:17][C:16]5[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=5)[N:10]=4)[CH2:7]3)[CH2:2]2)=[O:44])[CH:36]=1

Participants

5

Reactant 4

HCID 27605052-(Pyridin-3-yl)benzoic acidHCID 51056232-(Thiophen-2-yl)benzoic acidHCID 68156918(1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)quinoxalineHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 69931971(1R,6S)(2-Pyridin-3-yl-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 1, substituting (1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)quinoxaline (Intermediate 3) for (1R,6S)8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane and 2-pyridin-3-yl-benzoic acid for 2-thiophen-2-yl-benzoic acid. MS (ESI) mass calcd. for C26H23N5O, 421.49; m/z found, 422.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.79-8.44 (m, 2H), 8.27-8.26 (m, 9H), 6.83-6.13 (m, 2H), 4.78-3.77 (m, 4H), 3.73-3.32 (m, 2H), 3.18-2.58 (m, 2H), 2.00-1.47 (m, 2H).

Sources & evidence

ORD record
ord-9ca52210ebc343299793ed03f85d97e2
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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