Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 56592699 | HCID 56592699 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 56592772 | HCID 56592772 | 93.1% |
Reaction Steps
Methyl[1-(4-cyanophenyl)-7-methoxy-3-methyl-3H-pyrazolo[3,4-c]quinolin-8-yloxy]-(4-fluorophenyl)acetate (260 mg, 524 μmol) is dissolved in tetrahydrofuran and methanol (66 ml each). Sodium hydroxide solution (1.0 M, 1.58 ml, 1.58 mmol) is subsequently added dropwise. The reaction mixture is stirred at room temperature for 18 h. When the reaction is complete, the mixture is evaporated to dryness in vacuo, and the residue obtained is taken up in water (100 ml). The mixture is carefully acidified to pH 5 by addition of hydrochloric acid (1.0 M) and stirred for a further 30 min. The precipitate formed is filtered off with suction and rinsed with water. The filter cake is subsequently suspended in 2-propanol (5 ml), filtered off with suction again, and the residue is dried overnight in a high vacuum, giving [1-(4-cyanophenyl)-7-methoxy-3-methyl-3H-pyrazolo[3,4-c]quinolin-8-yl-oxy]-(4-fluorophenyl)acetic acid (235 mg, 488 μmol) as a solid having a melting point of 211.6° C. MS: 483.1 (M+H+), TLC (HPTLC): Rf=0.11 (ethanol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08802712B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-4fc22d1308394845b5c8494496913711 |
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| Source note | uspto-grants-2014_08 |
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