4-Phenylbenzoyl chloride → N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)biphenyl-4-carboxamide
Reaction equation
Cl.[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:34]=[CH:33][C:17]([CH2:18][NH:19][C:20]3[CH:32]=[CH:31][C:23]4[O:24][C:25]([CH3:30])([CH3:29])[O:26][C:27](=[O:28])[C:22]=4[CH:21]=3)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].[C:35]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:40]=[CH:39][C:38]([C:41](Cl)=[O:42])=[CH:37][CH:36]=1>>[CH2:2]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:14]2[CH:34]=[CH:33][C:17]([CH2:18][N:19]([C:20]3[CH:32]=[CH:31][C:23]4[O:24][C:25]([CH3:30])([CH3:29])[O:26][C:27](=[O:28])[C:22]=4[CH:21]=3)[C:41]([C:38]3[CH:39]=[CH:40][C:35]([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)=[CH:36][CH:37]=3)=[O:42])=[CH:16][CH:15]=2)=[CH:10][CH:11]=1)[CH2:3][CH2:4][CH3:5]Participants
3
Procedure
The titled compound was prepared following the procedure J using 6-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one hydrochloride and biphenyl-4-carbonyl chloride as a pale yellow oil (43%). 1H NMR (CDCl3, 300 MHz) δ 7.72 (brs, 1H), 7.53-7.27 (m, 15H), 7.17 (d, J=8.3 Hz, 2H), 6.98 (brd, J=8.7 Hz, 1H), 6.73 (d, J=8.7 Hz, 1H), 5.15 (s, 2H), 2.63 (t, J=7.5 Hz, 2H), 1.67 (s, 6H), 1.61 (m, 2H), 1.37 (m, 2H), 0.94 (t, J=7.2 Hz, 3H). HPLC, Rt: 6.07 min (Purity: 99.8%).
Sources & evidence
- ORD record
- ord-3c4281920465422193145ff2d1b2357a
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589232B2
Reaction notes
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