HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methanesulfonylacetic acid → Methyl 2-(4-((N-(3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-2-(methylsulfonyl)acetamido)methyl)phenyl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methanesulfonylacetic acid | HCID 3732841 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | Methyl 2-(4-((3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate | HCID 25106601 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 2-(4-((N-(3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-2-(methylsulfonyl)acetamido)methyl)phenyl)acetate | HCID 25106777 | 43.1% |
Reaction Steps
To a solution of the product from example 1 (221 mg) in DCM (10 mL) was added 2-(methylsulfonyl)acetic acid (66.4 mg) followed by TEA (0.201 mL) and HATU (201 mg). The reaction mixture was stirred at rt for 16 h then the solvents were evaporated. The crude product was purified by RPHPLC to afford the title compound (120 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08436178B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-290f78c7b34c42f68a0a10e1cfb90e94 |
| Source note | uspto-grants-2013_05 |