HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (4-ethoxy-2-hydroxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Ethoxysalicylic acid | HCID 82628 | — |
| 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 | 1-Methylspiro[chromeno[4,3-c]pyrazole-4,4'-piperidine] | HCID 58550738 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (4-ethoxy-2-hydroxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone | HCID 58551483 | 32% |
Reaction Conditions
| Temperature | 25 °C |
|---|
Reaction Steps
In a vial were added 4-ethoxy-2-hydroxybenzoic acid (0.40 mmol) followed by HATU (170 mg, 0.44 mmol), DMF (0.7 mL), and triethylamine (220 μL, 1.6 mmol). The mixture was stirred for 10 minutes before 1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (100 mg, 0.40 mmol) was added. The reaction mixture was allowed to stir at 25° C. for 12 hours before it was filtered and purified by HPLC (1-99%) MeOH:H2O to yield (4-ethoxy-2-hydroxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (53 mg, 32%). ESI-MS m/z calc. 419.5. found 420.4 (M+1)+. Retention time: 2.96 minutes (4 min run).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08598164B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-b68c4d73b4b2404482827635ae6f885c |
| Source note | uspto-grants-2013_12 |