HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-[2-(4'-Chloro-4-methoxy-biphen-2-yl)-quinolin-6-yl]-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid Ethyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 2-[2-(2-Bromo-phenyl)-quinolin-6-yl]-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylic Acid Ethyl Ester | HCID 68919212 | — |
| Reactant | 2-(4'-Chloro-4-methoxy-biphen-2-yl)-quinoline-6-carboxylic acid | HCID 86027313 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[2-(4'-Chloro-4-methoxy-biphen-2-yl)-quinolin-6-yl]-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid Ethyl Ester | HCID 131727379 | 40% |
Reaction Steps
The amine was reacted with Compound 525c (0.314 g, 0.805 mmol) in the presence of HBTU (0.32 g, 0.844 mmol) and DIEA (0.47 mL, 2.68 mmol) in DMF (10 mL), followed cyclization in AcOH (10 mL) according to procedure (2) and (3) in the preparation of Compound 477d. Separation by RP HPLC (from 20% of buffer B to 99% of buffer B) gave the title intermediate (0.19 g, 40%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07511145B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-0a2f227c2a164f239c7c766c164959dc |
| Source note | uspto-grants-2009_03 |