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

HRID 1193170Notes

Reaction equation

HRID 1193170 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][N:6]=[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:4]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[F:35][C:36]1[CH:37]=[CH:38][C:39]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)=[C:40]([CH:44]=1)[C:41](O)=[O:42].S1C=CC=C1C1C=CC=CC=1C(O)=O>>[F:35][C:36]1[CH:37]=[CH:38][C:39]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)=[C:40]([C:41]([N:14]2[CH2:13][CH2:12][C@@H:11]3[C@@H:16]([N:9]([C:5]4[N:4]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:8]=[CH:7][N:6]=4)[CH2:10]3)[CH2:15]2)=[O:42])[CH:44]=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 67116508HCID 67116508, compoundHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52919938(1R,6S)-3-{[5-Fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-8-[4-(trifluoromethyl)pyrimidin-2-yl]-3,8-diazabicyclo[4.2.0]octane

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-8-(4-(trifluoromethyl)pyrimidin-2-yl)-3,8-diazabicyclo[4.2.0]octane (Intermediate 27) 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 C20H17F4N7O, 447.40; m/z found 448.0 [M+H]+.

Sources & evidence

ORD record
ord-28293f2fa71d4ff1b7363a0edfac3752
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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