2-(Thiophen-2-yl)benzoic acid → HCID 52918935, compound

HRID 1193148Notes

Reaction equation

HRID 1193148 reaction equation
[C@@H:1]12[N:8]([C:9]3[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]([CH3:18])[CH3:17])[N:10]=3)[CH2:7][C@@H: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.[N:37]1[N:38]([C:42]2[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=2[C:44](O)=[O:45])[N:39]=[CH:40][CH:41]=1.S1C=CC=C1C1C=CC=CC=1C(O)=O>>[CH3:18][N:16]([CH3:17])[C:11]1[N:10]=[C:9]([N:8]2[C@@H:1]3[C@@H:6]([CH2:5][CH2:4][N:3]([C:44]([C:43]4[CH:47]=[CH:48][CH:49]=[CH:50][C:42]=4[N:38]4[N:39]=[CH:40][CH:41]=[N:37]4)=[O:45])[CH2:2]3)[CH2:7]2)[CH:14]=[C:13]([CH3:15])[N:12]=1

Participants

5

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acid2×HCID 68156860HCID 68156860, compoundHCID 68156918(1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)quinoxaline

Product 1

HCID 52918935HCID 52918935, compound

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-[4-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-6-methyl-pyrimidin-2-yl]-dimethyl-amine (Intermediate L) for (1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline and 2-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 14) for 2-thiophen-2-yl-benzoic acid. MS (ESI) mass calcd. for C22H26N8O, 418.501; m/z found 419.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.13-7.73 (m, 2H), 7.65-7.28 (m, 2H), 7.24-6.88 (m, 1H), 5.51-5.10 (m, 1H), 4.66-2.65 (m, 14H), 2.32-1.85 (m, 5H).

Sources & evidence

ORD record
ord-321edef380f945c1ba94d1947e99522a
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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