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]-(5-fluoro-2-[1,2,3]triazol-2-yl-phenyl)-methanone

HRID 1193150Notes

Reaction equation

HRID 1193150 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:40]=[CH:41][C:42]([N:48]2[N:52]=[CH:51][CH:50]=[N:49]2)=[C:43]([CH:47]=1)[C:44](O)=[O:45].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:44]([C:43]4[CH:47]=[C:39]([F:38])[CH:40]=[CH:41][C:42]=4[N:48]4[N:52]=[CH:51][CH:50]=[N:49]4)=[O:45])[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 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 69932407(1R,6S)-[4-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-6-trifluoromethyl-pyrimidin-2-yl]-dimethyl-amine

Product 1

HCID 52919051(1R,6S)-[8-(2-Dimethylamino-6-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-(5-fluoro-2-[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 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 C22H22F4N8O, 490.46; m/z found 491.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.17-7.73 (m, 2H), 7.44-7.09 (m, 2H), 7.07-6.58 (m, 1H), 5.87-5.54 (m, 1H), 4.51-3.30 (m, 7H), 3.20-2.75 (m, 7H), 2.28-1.87 (m, 2H).

Sources & evidence

ORD record
ord-06c58781ed624ff090dc8af3a5e49ba6
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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