HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 3,4-Dichloro-N-((1,1-dimethylethoxy)carbonyl)-D-phenylalanine | HCID 7015811 | — |
| Reactant | N-(2-(Piperazin-1-yl)phenyl)methanesulfonamide hydrochloride | HCID 21283546 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-carboxamide | HCID 10282776 | 113.3% |
| Product | n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide | HCID 21060073 | — |
Reaction Steps
N-[(1R)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide was prepared according to the procedure for Preparation XIX using (methylsulfonyl)(2-piperazinylphenyl)amine hydrochloride (800 mg, 2.8 mmol), N-Boc-D-3,4-dichlorophenylalanine (930 mg, 2.80 mmol) (Peptech), DIEA (480 μl, 2.80 mmol), EDC (1.66 g, 5.60 mmol), HOAT (400 mg, 3.0 mmol) and DMF (10 mL). The crude product was purified by flash chromatography (SiO2, 1:1 hexane:EtOAc) and concentrated in vacuo to afford the desired compound (1.0 g). MS (ESI, pos. ion) m/z: 571 (M+H), (ESI, neg. ion) m/z: 569 (M−H). Calc'd for C25H32Cl2N4O5S: 570.15.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07560460B2 |
| Source dataset | uspto-grants-2009_07 |
| ORD ID | ord-965145ba56bd43d9bbff5519d303565f |
| Source note | uspto-grants-2009_07 |