HCID 558187, compound → HCID 21898719, compound
Reaction equation
[CH2:1]([C:5]1[NH:9][N:8]=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([O:26]C)=[O:25])=[CH:14][CH:13]=1>>[CH2:1]([C:5]1[N:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:24]([OH:26])=[O:25])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[N:8]=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4]Participants
Procedure
Following General Procedure A, 5.0 g (39.9 mmol) of 5-butyl-1H-1,2,4-triazole was coupled with 12.2 g (39.9 mmol) of the alkylating reagent prepared in step 1 of Example 1 to give 3.1 g (22%) of a faster moving isomer: NMR (CDCl3) δ 0.90 (t, J=8 Hz, 3H), 1.29–1.45 (m, 2H), 1.63–1.76 (m, 2H), 2.71 (t, J=8 Hz, 2H), 3.62 (s, 3H), 5.34 (s, 2H), 7.14–7.20 (m, 2H), 7.24–7.33 (m, 3H), 7.40 (dt, J=8 and 2 Hz, 1H), 7.50 (dt, J=8 and 2 Hz, 1H), 7.82 (dd, J=8 and 2 Hz, 1H), 7.85 (s, 1H) and 3.7 g (26%) of a slower moving isomer: NMR (CDCl3) δ 0.92 (t, J=8 Hz, 3H), 1.31–1.46 (m, 2H), 1.66–1.79 (m, 2H), 2.73 (t, J=8 Hz, 2H), 3.62 (s, 3H), 5.28 (s, 2H), 7.21–7.34 (m, 5H), 7.39 (dt, J=8 and 2 Hz, 1H), 7.50 (dt, J=8 and 2 Hz, 1H), 7.83 (dd, J=8 and 2 Hz, 1H), 7.94 (s, 1H). The faster moving isomer was hydrolyzed to give 2.75 g (92%) of 4′-[(5-butyl-1H-1,2,4-triazol-1-yl)methyl]-[1,1′-biphenyl]-2-carboxylic acid as a colorless solid: NMR (DMSO-d6) δ 0.85 (t, J=8 Hz, 3H), 1.23–1.38 (m, 2H), 1.52–1.65 (m, 2H), 2.76 (t, J=7 Hz, 2H), 5.41 (s, 2H), 7.16–7.24 (m, 2H), 7.27–7.37 (m, 3H), 7.44 (dt, J=8 and 2 Hz, 1H), 7.56 (dt, J=8 and 2 Hz, 1H), 7.72 (dd, J=8 and 2 Hz, 1H), 7.86 (s, 1H); MS (FAB) m/e (rel intensity) 336 (100), 307 (7), 289 (7), 224 (8), 211 (100), 193 (9).
Workup
- customto give 3.1 g (22%) of
Sources & evidence
- ORD record
- ord-ffa5b0ec45c84f7f9b4548f214644a83
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07132437B2
Reaction notes
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