2-(Thiophen-2-yl)benzoic acid → (1R,6S)-(5-Fluoro-2-[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 1193147Notes

Reaction equation

HRID 1193147 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:38]=[CH:39][C:40]([N:46]2[N:50]=[CH:49][CH:48]=[N:47]2)=[C:41]([CH:45]=1)[C:42](O)=[O:43].S1C=CC=C1C1C=CC=CC=1C(O)=O>>[F:36][C:37]1[CH:38]=[CH:39][C:40]([N:46]2[N:50]=[CH:49][CH:48]=[N:47]2)=[C:41]([C:42]([N:17]2[CH2:16][CH2:15][C@@H:14]3[C@@H:19]([N:12]([C:4]4[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[N:5]=4)[CH2:13]3)[CH2:18]2)=[O:43])[CH:45]=1

Participants

5

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670869485-fluoro-2-(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 52918934(1R,6S)-(5-Fluoro-2-[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 5-fluoro-2-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 13) for 2-thiophen-2-yl-benzoic acid. MS (ESI) mass calcd. for C21H19F4N7O, 461.422; m/z found 462.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.09-7.71 (m, 2H), 7.55-6.50 (m, 3H), 6.14 (d, J=81.2, 1H), 4.76-3.62 (m, 6H), 3.50-2.85 (m, 2H), 2.78-1.92 (m, 5H).

Sources & evidence

ORD record
ord-23dd4d4e83fb4f2597ece95e101ec450
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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