o-Phenylbenzoic acid → (1S,6R)Biphenyl-2-yl-[8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-methanone
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)[N:3]=1.[C:17]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:18]([C:23](O)=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=1.S1C=CC=C1C1C=CC=CC=1C(O)=O>>[C:17]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([N:14]1[CH2:13][CH2:12][C@H:11]2[C@H:16]([N:9]([C:4]3[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=3)[CH2:10]2)[CH2:15]1)=[O:24]Participants
4
Procedure
The title compound was prepared in a manner analogous to Example 1, substituting (1S,6R)8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane 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 C25H26N4O, 398.5; m/z found 399.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.56-7.25 (m, 7H), 7.24-6.72 (m, 2H), 6.44-6.17 (m, 1H), 4.57-3.20 (m, 6H), 3.01-2.40 (m, 2.5H), 2.37-2.00 (m, 6H), 1.38-1.31 (m, 1.5H).
Sources & evidence
- ORD record
- ord-4775fe3c93b348bc9b60523fd9786021
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680275B2
Reaction notes
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