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

HRID 1193142Notes

Reaction equation

HRID 1193142 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([N:12]2[C@@H:19]3[C@@H:14]([CH2:15][CH2:16][NH:17][CH2:18]3)[CH2:13]2)[CH:3]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[N:36]1[N:37]([C:41]2[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=2[C:43](O)=[O:44])[N:38]=[CH:39][CH:40]=1.S1C=CC=C1C1C=CC=CC=1C(O)=O>>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[N:5]=[C:4]([N:12]2[C@@H:19]3[C@@H:14]([CH2:15][CH2:16][N:17]([C:43]([C:42]4[CH:46]=[CH:47][CH:48]=[CH:49][C:41]=4[N:37]4[N:38]=[CH:39][CH:40]=[N:36]4)=[O:44])[CH2:18]3)[CH2:13]2)[CH:3]=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 68156957(1R,6S)-8-(6-Methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52918815(1R,6S)-[8-(6-Methyl-2-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)-8-(6-methyl-2-trifluoromethyl-pyrimidin-4-yl)-3,8-diaza-bicyclo[4.2.0]octane (Intermediate 9) 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 O21H20F3N7O, 443.43; m/z found 444.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.16-5.81 (m, 7H), 4.84-1.60 (m, 13H).

Sources & evidence

ORD record
ord-4fe284cdfbfc426293472ddb6834fa32
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

Loading…