2-(Thiophen-2-yl)benzoic acid → HCID 52920287, compound

HRID 1193183Notes

Reaction equation

HRID 1193183 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[C@@H:15]3[C@@H:10]([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:9]2)[CH:5]=[N:4][CH:3]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[F:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([N:42]2[N:46]=[CH:45][CH:44]=[N:43]2)[C:34]=1[C:35](O)=[O:36].S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[F:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([N:42]2[N:46]=[CH:45][CH:44]=[N:43]2)[C:34]=1[C:35]([N:13]1[CH2:12][CH2:11][C@@H:10]2[C@@H:15]([N:8]([C:6]3[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[CH2:9]2)[CH2:14]1)=[O:36]

Participants

6

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670866272-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid2×HCID 67116766(1R,6S)-8-(6-Methylpyrazin-2-yl)-3,8-diazabicyclo[4.2.0]octaneHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52920287HCID 52920287, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-8-(6-methylpyrazin-2-yl)-3,8-diazabicyclo[4.2.0]octane (Intermediate 30) 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 C20H21N7O, 375.44; m/z found 376.1 [M+H]+. 1H NMR (CD3OD): 8.08-7.75 (m, 3H), 7.68-7.37 (m, 4H), 7.33-6.82 (m, 1H), 4.70-3.78 (m, 5H), 3.64-2.97 (m, 3H), 2.43-2.01 (m, 5H). MS (ESI) mass calcd. For C20H20FN7O, 393.43; m/z found 394.1 [M+H]+. 1H NMR (CD3OD): 7.99-7.75 (m, 3H), 7.68-6.92 (m, 4H), 4.71-3.35 (m, 7H), 3.16-2.98 (m, 1H), 2.54-1.85 (m, 5H).

Sources & evidence

ORD record
ord-0f36d6a43b844bccbffcfe103b79aca4
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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