3-Cyclopentylpropionyl chloride → N-{4-[(4-butylphenyl)ethynyl]benzyl}-3-cyclopentyl-N-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)methyl]propanamide
Reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][NH:18][CH2:19][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:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH:35]1([CH2:40][CH2:41][C:42](Cl)=[O:43])[CH2:39][CH2:38][CH2:37][CH2:36]1>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][N:18]([CH2:19][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:42](=[O:43])[CH2:41][CH2:40][CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
The titled compound was prepared following the procedure B using 6-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]-2,2-dimethyl-4H-1,3-benzodioxin-4-one and 3-cyclopentylpropanoyl chloride as a colorless oil (72%). 1H NMR (CDCl3, 300 MHz) δ 7.74 (m, 1H), 7.50 (m, 2H), 7.43 (m, 2H), 7.35-7.21 (m, 1H), 7.20-6.85 (m, 5H), 4.56 (m, 2H), 4.52-4.40 (m, 2H), 2.61 (t, J=7.5 Hz, 2H), 2.42 (m, 2H), 1.80-1.62 (m, 11H), 1.61-1.30 (m, 8H). 1.18-1.00 (m, 2H), 0.92 (t, J=7.2 Hz, 3H). HPLC, Rt: 6.11 min (Purity; 98.7%).
Sources & evidence
- ORD record
- ord-179197b02dd84f7681ddb3a915885ffe
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589232B2
Reaction notes
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