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

HRID 1193144Notes

Reaction equation

HRID 1193144 reaction equation
[C@@H:1]12[N:8]([C:9]3[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[C:11]([N:19]([CH3:21])[CH3:20])[N:10]=3)[CH2:7][C@@H:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[F:38][C:39]1[CH:47]=[CH:46][CH:45]=[C:44]([N:48]2[N:52]=[CH:51][CH:50]=[N:49]2)[C:40]=1[C:41](O)=[O:42].S1C=CC=C1C1C=CC=CC=1C(O)=O>>[CH3:20][N:19]([CH3:21])[C:11]1[N:10]=[C:9]([N:8]2[C@@H:1]3[C@@H:6]([CH2:5][CH2:4][N:3]([C:41]([C:40]4[C:44]([N:48]5[N:52]=[CH:51][CH:50]=[N:49]5)=[CH:45][CH:46]=[CH:47][C:39]=4[F:38])=[O:42])[CH2:2]3)[CH2:7]2)[CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[N:12]=1

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 69932407(1R,6S)-[4-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-6-trifluoromethyl-pyrimidin-2-yl]-dimethyl-amine

Product 1

HCID 52918817(1R,6S)-[8-(2-Dimethylamino-6-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-(2-fluoro-6-[1,2,3]triazol-2-yl-phenyl)-methanone

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-[4-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-6-trifluoromethyl-pyrimidin-2-yl]-dimethyl-amine (Intermediate 11) for (1R,6S)8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane and 6-fluoro-2-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 15) for 2-thiophen-2-yl-benzoic acid. MS (ESI) mass calcd. for C22H22F4N8O, 490.46; m/z found 491.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.98-7.73 (m, 2H), 7.52-7.28 (m, 2H), 7.19-6.73 (m, 1H), 5.88-5.43 (m, 1H), 4.50-4.24 (m, 1H), 4.21-3.85 (m, 5H), 3.82-3.40 (m, 2H), 3.24-2.77 (m, 6H), 2.31-1.91 (m, 2H).

Sources & evidence

ORD record
ord-54c639e787cb49d28a2218f0fe1858cd
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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