2-(Thiophen-2-yl)benzoic acid → HCID 52920412, compound

HRID 1193184Notes

Reaction equation

HRID 1193184 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[C:37]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)=[C:38]([CH:42]=[CH:43][CH:44]=1)[C:39](O)=[O:40].S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[F:35][C:36]1[C:37]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)=[C:38]([C:39]([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:40])[CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670865493-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 52920412HCID 52920412, 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 3-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 50) 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): 8.27-8.14 (m, 1H), 8.08-7.58 (m, 5H), 7.48-6.45 (m, 4H), 4.83-4.54 (m, 1H), 4.25-3.97 (m, 3H), 3.74-3.63 (m, 1H), 3.43-3.37 (m, 1H), 3.19-3.06 (m, 2H), 2.27-1.82 (m, 2H).

Sources & evidence

ORD record
ord-09c422e550b840a983565c383ed6f701
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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