o-Phenylbenzoic acid → Biphenyl-2-yl-[8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-methanone
Reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]3[CH:20]4[CH:15]([CH2:16][CH2:17][NH:18][CH2:19]4)[CH2:14]3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[C:37]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:38]([C:43](O)=[O:44])=[CH:39][CH:40]=[CH:41][CH:42]=1.S1C=CC=C1C1C=CC=CC=1C(O)=O>>[C:37]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]([N:18]1[CH2:17][CH2:16][CH:15]2[CH:20]([N:13]([C:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:12]=[CH:11][N:10]=3)[CH2:14]2)[CH2:19]1)=[O:44]Participants
5
Reactant 4
Product 1
Procedure
The title compound was prepared in a manner analogous to Example 1, substituting 8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane (Intermediate 6) for (1R,6S)8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane and biphenyl-2-carboxylic acid for 2-thiophen-2-yl-benzoic acid. MS (ESI) mass calcd. for C29H26N4O, 446.54; m/z found, 447.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.44-7.28 (m, 13H), 7.27-6.79 (m, 3H), 4.70-3.66 (m, 4H), 3.59-2.31 (m, 3H), 2.19-0.93 (M, 3H).
Sources & evidence
- ORD record
- ord-88d4df4bb25c490ea93894cf04120135
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680275B2
Reaction notes
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