2-(Thiophen-2-yl)benzoic acid → (1R,6S)-(2-Fluoro-6-[1,2,3]triazol-2-yl-phenyl)-[8-(6-methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-methanone

HRID 1193140Notes

Reaction equation

HRID 1193140 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([N:12]2[C@@H:19]3[C@@H:14]([CH2:15][CH2:16][NH:17][CH2:18]3)[CH2:13]2)[CH:3]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[F:36][C:37]1[CH:45]=[CH:44][CH:43]=[C:42]([N:46]2[N:50]=[CH:49][CH:48]=[N:47]2)[C:38]=1[C:39](O)=[O:40].S1C=CC=C1C1C=CC=CC=1C(O)=O>>[F:36][C:37]1[CH:45]=[CH:44][CH:43]=[C:42]([N:46]2[N:50]=[CH:49][CH:48]=[N:47]2)[C:38]=1[C:39]([N:17]1[CH2:16][CH2:15][C@@H:14]2[C@@H:19]([N:12]([C:4]3[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[N:5]=3)[CH2:13]2)[CH2:18]1)=[O:40]

Participants

5

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670866272-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid2×HCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octaneHCID 68156957(1R,6S)-8-(6-Methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52918692(1R,6S)-(2-Fluoro-6-[1,2,3]triazol-2-yl-phenyl)-[8-(6-methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-methanone

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-[8-(6-methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]octane (Intermediate 9) for (1R,6S)8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane and 3-fluoro-6-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 15) for 2-thiophen-2-yl-benzoic acid. Additionally, the reaction time was shortened to 30 minutes. MS (ESI) mass calcd. for C21H19F4N7O, 461.42; m/z found 462.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.89-7.60 (m, 3H), 7.57-7.27 (m, 1H), 7.20-6.99 (m, 1H), 6.90-6.55 (m, 1H), 4.85 (5, br, 0.35H), 4.50-3.12 (m, 7H), 2.97-2.57 (m, 1.65H), 2.44-2.04 (m, 7H).

Sources & evidence

ORD record
ord-a71c2fc3b3144c4493a15657c2b3d6b3
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

Loading…