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

HRID 1193171Notes

Reaction equation

HRID 1193171 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:44]=[CH:43][CH:42]=[C:41]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)[C:37]=1[C:38](O)=[O:39].S1C=CC=C1C1C=CC=CC=1C(O)=O>>[F:35][C:36]1[CH:44]=[CH:43][CH:42]=[C:41]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)[C:37]=1[C:38]([N:14]1[CH2:13][CH2:12][C@@H:11]2[C@@H:16]([N:9]([C:5]3[N:4]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:8]=[CH:7][N:6]=3)[CH2:10]2)[CH2:15]1)=[O:39]

Participants

5

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670866272-Fluoro-6-(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 52919939(1R,6S)-3-{[2-Fluoro-6-(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 2-fluoro-6-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 15) 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-5d1a74b001b54c04a49836ff363a9265
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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