Butyl bromide → 3-butyl-2-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1H-pyrazol-3-yl]-3,5-dihydro-imidazol-4-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]3[NH:25][C:24](=[O:26])[CH2:23][N:22]=3)[C:9]=2[CH2:27][CH3:28])=[CH:4][CH:3]=1.[CH2:29](Br)[CH2:30][CH2:31][CH3:32]>>[CH2:29]([N:25]1[C:24](=[O:26])[CH2:23][N:22]=[C:21]1[C:10]1[C:9]([CH2:27][CH3:28])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[N:11]=1)[CH2:30][CH2:31][CH3:32]Participants
3
Procedure
Compound 30 was synthesized from 26 (102 mg, 0.23 mmol) and n-butyl bromide (500 mg, 3.65 mmol) as a white solid (55 mg, 49%) in a manner similar to that described in Example 59. 1H NMR (400 MHz, CDCl3) δ 7.44 (d, 1H), 7.30 (d, 2H), 7.25 (dd, 1H), 7.17 (d, 1H), 7.09 (d, 2H), 4.83 (s, 0.82H), 4.45 (s, 1.18H), 3.80 (s, 1.18H), 3.67 (s, 0.82H), 2.65 (q, 2H), 1.69 (br s, 2H), 1.42-1.25 (m, 2H), 1.13 (t, 3H), 0.97-0.86 (m, 3H); ESMS m/: 489.1 (M+1).
Sources & evidence
- ORD record
- ord-bd898e98ee534a4ead6201c7b5ac768d
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354442B2
Reaction notes
Loading…