(E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine → (E)-2-[3-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-3-oxopropyl]benzoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14]([OH:16])=O)=[O:5])[CH3:2].[CH:17]1([C:21]2[N:22]=[C:23](/[CH:26]=[CH:27]/[C:28]3[CH:29]=[C:30]([NH2:34])[CH:31]=[CH:32][CH:33]=3)[S:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14]([NH:34][C:30]1[CH:31]=[CH:32][CH:33]=[C:28](/[CH:27]=[CH:26]/[C:23]2[S:24][CH:25]=[C:21]([CH:17]3[CH2:20][CH2:19][CH2:18]3)[N:22]=2)[CH:29]=1)=[O:16])[CH3:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution composed of 0.44 g of 2-(ethoxycarbonyl)benzenepropanoic acid and 25 ml of methylene chloride was added to a solution composed of 0.51 g of (E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine, 0.4 g of N-ethyl-N-(dimethylaminopropyl)carbodiimide, 1.0 g of 4-dimethylaminopyridine and 25 ml of methylene chloride at 0° C. After 16 hr., the reaction mixture was washed with 30 ml of water, dried (MgSO4) and the solvents removed by rotary evaporation. The residual materials were recrystallized from ethyl ether to yield 0.87 g of (E)-2-[3-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-3-oxopropyl]benzoic acid ethyl ester; m.p.110°-111° C.
Workup
- additionwas added to a solution
- wash, the reaction mixture was washed with 30 ml of water
- dry with materialdried (MgSO4)
- customthe solvents removed by rotary evaporation
- customThe residual materials were recrystallized from ethyl ether
Sources & evidence
- ORD record
- ord-8ad9756cebe540d6a69be0934337860b
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05273986
Reaction notes
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