Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 3-Pentanamine | HCID 12019 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 90370193 | HCID 90370193 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 90370232 | HCID 90370232 | — |
Reaction Steps
A mixture of 8.00 g of methyl 4-[2-(4-{[(2-{[3-(chloromethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate, 4.8 mL of pentan-3-amine, 3.5 mL of N-ethyl-N-isopropylpropan-2-amine, and 80 mL of DMF was stirred for 13 hours at 80° C. Ethyl acetate and water were added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (2% methanol/chloroform), thereby obtaining 6.57 g of methyl 4-{2-[4-({[2-({3-[(pentan-3-ylamino)methyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09062032B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-ea78eb27c535405789ecee6a12de4974 |
|---|
| Source note | uspto-grants-2015_06 |
|---|