1-(Bromomethyl)-2,3-dichlorobenzene → 7-[2-Methyl-3-(trifluoromethyl)benzyl]-3-pyridin-2-yl-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one
Reaction equation
[N:1]1[CH:6]=[CH:5]N=[CH:3][C:2]=1[C:7]1[N:11]2[CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:10]2=[N:9][N:8]=1.Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[C:20]=1[CH3:29].Br[CH2:31]C1C=CC=C(Cl)C=1Cl>>[CH3:29][C:20]1[C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:14]1[CH2:13][CH2:12][N:11]2[C:7]([C:2]3[CH:3]=[CH:31][CH:5]=[CH:6][N:1]=3)=[N:8][N:9]=[C:10]2[C:15]1=[O:16]Participants
4
Reactant 3
Product 1
Procedure
Example 10 was made in a manner analogous to Example 2 substituting Intermediate 2 for Intermediate 1 and 1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene for 1-(bromomethyl)-2,3-dichlorobenzene to provide the desired compound as a white solid (53 mg, 75%). MS (ESI): mass calcd. for C19H16F3N5O, 387.1; m/z found, 388.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 8.78-8.66 (m, 1H), 8.29 (d, J=7.9 Hz, 1H), 8.05 (dt, J=7.8, 1.7 Hz, 1H), 7.63 (dd, J=16.8, 7.8 Hz, 2H), 7.57 (ddd, J=7.6, 4.9, 1.1 Hz, 1H), 7.40 (t, J=7.8 Hz, 1H), 4.87 (dd, J=15.9, 9.8 Hz, 4H), 3.85-3.74 (m, 2H), 2.41 (s, 3H).
Sources & evidence
- ORD record
- ord-1fecb583955e4c5e9cf4faecf4825323
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040534B2
Reaction notes
Loading…