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

HRID 1193145Notes

Reaction equation

HRID 1193145 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[N:36]([C:40]2[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=2[C:42](O)=[O:43])[N:37]=[CH:38][CH:39]=1.S1C=CC=C1C1C=CC=CC=1C(O)=O>>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:17]=[CH:18][C:9]=1[N:8]1[C@@H:1]2[C@@H:6]([CH2:5][CH2:4][N:3]([C:42]([C:41]3[CH:45]=[CH:46][CH:47]=[CH:48][C:40]=3[N:36]3[N:37]=[CH:38][CH:39]=[N:35]3)=[O:43])[CH2:2]2)[CH2:7]1

Participants

5

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acid2×HCID 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 52918819(1R,6S)-(8-Quinoxalin-2-yl-3,8-diaza-bicyclo[4.2.0]oct-3-yl)-(2-[1,2,3]triazol-2-yl-phenyl)methanone

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting 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-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 14) for 2-thiophen-2-yl-benzoic acid. MS (ESI) mass calcd. for C23H21N7O, 411.47; m/z found 412.2 [M+H]+.

Sources & evidence

ORD record
ord-5dde4fda4a0543308dcc2dd6a3c45de7
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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