HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → Methyl 2-(4-((N-(3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-3-(piperidin-1-yl)propanamido)methyl)phenyl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 1-Piperidinepropanoic acid | HCID 117782 | — |
| 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-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate | HCID 68430910 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 2-(4-((N-(3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl)-3-(piperidin-1-yl)propanamido)methyl)phenyl)acetate | HCID 25107147 | 11.5% |
Reaction Steps
To the product from step (v) of example 29 (480 mg, 1.04 mmol) in DMF (5 mL), 3-(piperidin-1-yl)propanoic acid (196 mg, 1.25 mmol) and HATU (475 mg, 1.25 mmol) were added at rt and stirred for 2 hours. After adding 1 mL of methanol, the crude product was purified by RPHPLC and the resulting residue was triturated with diethyl ether: EtOAc (5:1). The suspension was filtered to afford the title compound as a white solid (72 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08436178B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-e38ab1a51ad846b68ddea09f89c0491a |
| Source note | uspto-grants-2013_05 |