2-Thiopheneacetyl chloride → Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(2-thienylacetyl)amino]-2 fluorobenzoate
Reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:31]=[CH:30][C:16]([CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([O:26][CH3:27])=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[S:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[CH2:37][C:38](Cl)=[O:39]>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][N:18]([C:38](=[O:39])[CH2:37][C:33]3[S:32][CH:36]=[CH:35][CH:34]=3)[C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([O:26][CH3:27])=[O:25])=[CH:30][CH:31]=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 methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate and 2-thiophenacetyl chloride as a pink oil (92%). 1H NMR (CDCl3, 300 MHz) δ 7.61 (dd, J=6.2, 2.5 Hz, 1H), 7.44 (m, 4H), 7.17 (m, 5H), 7.07 (m, 1H), 6.97-6.88 (m, 2H), 6.70 (d, J=3.0 Hz, 1H), 4.90 (s, 2H), 3.94 (s, 31), 3.65 (s, 2H), 2.63 (t, J=7.5 Hz, 2H), 1.61 (m, 2H), 1.37 (m, 2H), 0.94 (t, J=7.4 Hz, 3H). M1(ESI): 540.1. HPLC, Rt: 5.72 min (Purity: 99.2%).
Sources & evidence
- ORD record
- ord-8e2d32d03e6b4d0db52d787296364938
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589232B2
Reaction notes
Loading…