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

HRID 1193143Notes

Reaction equation

HRID 1193143 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.[N:38]1[N:39]([C:43]2[CH:51]=[CH:50][CH:49]=[CH:48][C:44]=2[C:45](O)=[O:46])[N:40]=[CH:41][CH:42]=1.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:45]([C:44]4[CH:48]=[CH:49][CH:50]=[CH:51][C:43]=4[N:39]4[N:40]=[CH:41][CH:42]=[N:38]4)=[O:46])[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 213135922-(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 52918816(1R,6S)-[8-(2-Dimethylamino-6-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-(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 2-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 14) for 2-thiophen-2-yl-benzoic acid. Additionally, the reaction time was shortened to 30 minutes. MS (ESI) mass calcd. for O22H−23F3N8O, 472.47; m/z found 473 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.19-6.80 (m, 7H), 4.49-3.78 (m, 5H), 3.75-3.30 (m, 2H), 3.22-3.10 (m, 2H), 3.06-2.74 (m, 5H), 2.24-1.87 (m, 2H).

Sources & evidence

ORD record
ord-612803b030174221a2adb72773114f1d
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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