2-(Thiophen-2-yl)benzoic acid → HCID 52920166, compound

HRID 1193180Notes

Reaction equation

HRID 1193180 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:35]=[CH:36][C:37]([N:43]2[N:47]=[CH:46][CH:45]=[N:44]2)=[C:38]([CH:42]=1)[C:39](O)=[O:40].S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[F:33][C:34]1[CH:35]=[CH:36][C:37]([N:43]2[N:47]=[CH:46][CH:45]=[N:44]2)=[C:38]([C:39]([N:14]2[CH2:13][CH2:12][C@@H:11]3[C@@H:16]([N:9]([C:5]4[C:4]([CH3:17])=[N:3][CH:2]=[CH:7][N:6]=4)[CH2:10]3)[CH2:15]2)=[O:40])[CH:42]=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 67116879HCID 67116879, compoundHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52920166HCID 52920166, 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 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 C20H20FN7O, 393.43; m/z found 394.1 [M+H]+. 1H NMR (CD3OD): 8.10-8.01 (m, 1H), 7.97-7.88 (m, 2H), 7.83-7.74 (m, 1H), 7.67-7.61 (m, 1H), 7.47-7.22 (m, 2H), 4.52-4.30 (m, 2H), 4.22-3.83 (m, 2H), 3.75-3.11 (m, 3H), 2.72-2.31 (m, 4H), 2.18-1.50 (m, 2H).

Sources & evidence

ORD record
ord-abf864d8bd254d0ab96d88b3ef1a129c
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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