6-Amino1-[3-(4-cyano-phenyl)propionyl]-1,2,3,4-tetrahydro-quinoline → 1-[3-(4-Cyano-phenyl)propionyl]-6-(4-amino-3,5-dichloro-phenyl-sulphonamido)-1,2,3,4-tetrahydro-quinoline
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:23])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[CH2:7][CH2:6][CH2:5]2.[NH2:24][C:25]1[C:30]([Cl:31])=[CH:29][C:28]([S:32](Cl)(=[O:34])=[O:33])=[CH:27][C:26]=1[Cl:36]>N1C=CC=CC=1>[C:21]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][C:12]([N:8]2[C:9]3[C:4](=[CH:3][C:2]([NH:1][S:32]([C:28]4[CH:29]=[C:30]([Cl:31])[C:25]([NH2:24])=[C:26]([Cl:36])[CH:27]=4)(=[O:34])=[O:33])=[CH:11][CH:10]=3)[CH2:5][CH2:6][CH2:7]2)=[O:23])=[CH:20][CH:19]=1)#[N:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1.0 g 6-amino-1-[3-(4-cyano-phenyl)propionyl]-1,2,3,4-tetrahydro-quinoline (see Example, 5) are dissolved in 8 ml of pyridine, combined with 1 g of 4-amino-3,5-dichloro-phenylsulphonic acid chloride in batches and then heated for 40 minutes to 100° C. Then the solvent is eliminated, the residue is triturated with 1N hydrochloric acid and extracted with methylene chloride. The organic phase is dried over sodium sulphate and concentrated by evaporation.
Workup
- temperatureheated for 40 minutes to 100° C
- customthe residue is triturated with 1N hydrochloric acid
- extractionextracted with methylene chloride
- dry with materialThe organic phase is dried over sodium sulphate
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-f0751c7240fd4926a769eea56a05247b
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300342B1
Reaction notes
Loading…