Veratraldehyde → 1-Butyl-3-(4-chloro-phenyl)-6-(3,4-dimethoxy-benzyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene
Reaction equation
[CH2:1]([N:5]1[C:14]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9][C:8]=2[C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[N:6]1)[CH2:2][CH2:3][CH3:4].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH:27]=O>>[CH2:1]([N:5]1[C:14]2[CH2:13][CH2:12][N:11]([CH2:27][C:26]3[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:24]([O:23][CH3:22])[CH:25]=3)[CH2:10][CH2:9][C:8]=2[C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[N:6]1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
The title compound (8 mg) was prepared from 1-butyl-3-(4-chloro-phenyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene (Example 67, 14 mg) using 3,4-dimethoxy-benzaldehyde (0.2 mmol) in place of formaldehyde. MS (ESI): exact mass calculated for C26H32ClN3O2, 453.22; found, m/z 454.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.38 (d, J=8.4 Hz, 2H), 7.28 (d, J=8.4 Hz, 2H), 7.20 (s, 1H), 6.91-6.90 (br m, 1H), 6.81 (d, J=8.2 Hz, 1H), 6.75 (d, J=8.2 Hz, 1H), 3.98 (t, J=7.3 Hz, 2H), 3.82 (d, J=7.0 Hz, 6H), 3.66 (s, 2H), 2.78-2.72 (br m, 8H), 1.67 (m, 2H), 1.27 (m, 2H), 0.86 (t, J=7.3 Hz, 6H).
Sources & evidence
- ORD record
- ord-6fbf8931c025466f91a15c8e38ccc66f
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07402680B2
Reaction notes
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