2-(Thiophen-2-yl)benzoic acid → HCID 69932186, compound

HRID 1193186Notes

Reaction equation

HRID 1193186 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.[F:35][C:36]1[CH:37]=[CH:38][C:39]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)=[C:40]([CH:44]=1)[C:41](O)=[O:42].S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[F:35][C:36]1[CH:37]=[CH:38][C:39]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)=[C:40]([C:41]([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:42])[CH:44]=1

Participants

6

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670869485-fluoro-2-(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 69932186HCID 69932186, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 5-fluoro-2-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 13) for 2-thiophen-2-yl-benzoic acid. DCM was used in place of DMF. MS (ESI) mass calcd. For C23H20FN7O, 429.46; m/z found 430.1 [M+H]+. 1H NMR (CD3OD): 8.60-8.30 (m, 1H), 8.04-7.33 (m, 8H), 7.24-6.55 (m, 1H), 5.15-4.72 (m, 1H), 4.54-4.43 (m, 2H), 4.32-3.53 (m, 4H), 3.26-3.16 (m, 1H), 2.36-1.91 (m, 2H).

Sources & evidence

ORD record
ord-488cd6d58d4d45529909bb8d1021bce4
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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