2-(Thiophen-2-yl)benzoic acid → HCID 52920411, compound

HRID 1193185Notes

Reaction equation

HRID 1193185 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:44]=[CH:43][CH:42]=[C:41]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)[C:37]=1[C:38](O)=[O:39].S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[F:35][C:36]1[CH:44]=[CH:43][CH:42]=[C:41]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)[C:37]=1[C:38]([N:3]1[CH2:4][CH2:5][C@@H:6]2[C@@H:1]([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]2)[CH2:2]1)=[O:39]

Participants

6

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670866272-Fluoro-6-(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 52920411HCID 52920411, 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 2-fluoro-6-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 15) 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 430.2 [M+H]+. 1H NMR (CD3OD): 8.42-7.97 (m, 2H), 7.88-7.44 (m, 5H), 7.39-6.20 (m, 3H), 5.08-4.67 (m, 1H), 4.41-3.44 (m, 6H), 3.25-3.07 (m, 1H), 2.39-1.86 (m, 2H).

Sources & evidence

ORD record
ord-580820fafc9b46c09e457ce92352f430
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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