HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-(7-Amino-6-bromo-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-cyclohexanecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 66738157 | HCID 66738157 | — |
| Solvent | Water | HCID 962 | — |
| Product | 4-(7-Amino-6-bromo-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-cyclohexanecarboxylic acid | HCID 58173446 | 34.6% |
Reaction Steps
4-{7-[Bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-6-bromo-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester (100 mg, 0.135 mmol) in 2:1 MeOH:H2O (3 mL) was treated with 2N NaOH(aq) (0.5 mL). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was treated with 1N hydrochloride solution (2 ml) at 65° C. for 4 h. The reaction mixture was concentrated and purified by prep-LC to afford the title compound (21.8 mg): LC/MS RT=3.57 min. Mass calculated for, M+H 466.08, observed 466.08.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08591943B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-df32b7aa205a4084b73565ef474cd4e1 |
| Source note | uspto-grants-2013_11 |