2-(Thiophen-2-yl)benzoic acid → (1R,6S)-3-{[5-Methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-8-[4-(trifluoromethyl)pyridin-2-yl]-3,8-diazabicyclo[4.2.0]octane

HRID 1193195Notes

Reaction equation

HRID 1193195 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)=[C:7]([CH:11]=1)[C:8]([OH:10])=O.S1C=CC=C1C1C=CC=CC=1C(O)=O.[F:31][C:32]([F:48])([F:47])[C:33]1[CH:38]=[CH:37][N:36]=[C:35]([N:39]2[C@@H:46]3[C@@H:41]([CH2:42][CH2:43][NH:44][CH2:45]3)[CH2:40]2)[CH:34]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)=[C:7]([C:8]([N:44]2[CH2:43][CH2:42][C@@H:41]3[C@@H:46]([N:39]([C:35]4[CH:34]=[C:33]([C:32]([F:48])([F:31])[F:47])[CH:38]=[CH:37][N:36]=4)[CH2:40]3)[CH2:45]2)=[O:10])[CH:11]=1

Participants

5

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670865655-Methoxy-2-(2H-1,2,3-triazol-2-yl)benzoic acidHCID 67116759(1R,6S)-8-(4-(Trifluoromethyl)pyridin-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 67116628(1R,6S)-3-{[5-Methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-8-[4-(trifluoromethyl)pyridin-2-yl]-3,8-diazabicyclo[4.2.0]octane

Procedure

The title compound was prepared in a manner analogous to Example 1 substituting 5-methoxy-2-(2H-1,2,3-triazol-2-yl)benzoic acid for 2-thiophen-2-yl-benzoic acid and Intermediate 44 for (1R,6S)8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane. MS (ESI) mass calcd. for C22H21F3N6O2, 458.5; m/z found, 459.2 [M+H]+.

Sources & evidence

ORD record
ord-fb1e5ecd0e834befa30423eeb97b618d
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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