2-(Thiophen-2-yl)benzoic acid → HCID 52920165, compound

HRID 1193179Notes

Reaction equation

HRID 1193179 reaction equation
C[C:2]1[N:3]=[CH:4][C:5]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)=[N:6][C:7]=1C.[CH3:17]C1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[F:33][C:34]1[CH:42]=[CH:41][CH:40]=[C:39]([N:43]2[N:47]=[CH:46][CH:45]=[N:44]2)[C:35]=1[C:36](O)=[O:37].S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[F:33][C:34]1[CH:42]=[CH:41][CH:40]=[C:39]([N:43]2[N:47]=[CH:46][CH:45]=[N:44]2)[C:35]=1[C:36]([N:14]1[CH2:13][CH2:12][C@@H:11]2[C@@H:16]([N:9]([C:5]3[C:4]([CH3:17])=[N:3][CH:2]=[CH:7][N:6]=3)[CH2:10]2)[CH2:15]1)=[O:37]

Participants

6

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670866272-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid2×HCID 67116879HCID 67116879, compoundHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52920165HCID 52920165, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-8-(3-methylpyrazin-2-yl)-3,8-diazabicyclo[4.2.0]octane (Intermediate 31) 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 C20H20FN7O, 393.43; m/z found 394.1 [M+H]+. 1H NMR (CD3OD): 7.99-7.79 (m, 4H), 7.72-7.59 (m, 2H), 7.38-7.21 (m, 1H), 4.63-4.01 (m, 4H), 3.82-3.24 (m, 3H), 2.74-2.25 (m, 4H), 2.16-1.29 (m, 2H).

Sources & evidence

ORD record
ord-e4d768559b0642cea19fc1fa2d3b25fa
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

Loading…