Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | HCID 57731556 | HCID 57731556 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 57731586 | HCID 57731586 | 25.4% |
Reaction Steps
5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-(toluene-4-sulfonyl)-2H-pyrazole-3-carboxylic acid dimethylamide (90 mg, 0.174 mmol) was dissolved in methanol (0.5 mL) and dimethylformamide (0.5 mL) and 50% w/v aqueous potassium hydroxide (0.5 mL) was added. After 3 hours, acetic acid (0.5 mL) was added and the mixture diluted with water. The solids were collected by filtration and the material purified by preparative HPLC to afford 5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2H-pyrazole-3-carboxylic acid dimethylamide (16.0 mg, 25.4%) 1H-NMR (500 MHz, dimethylsulfoxide-d6, 70° C.) δ 3.06-3.15 (s, 6H), 3.83 (s, 3H), 6.98 (br s, 1H), 7.07 (t, J=7.5 Hz, 1H), 7.14 (d, J=8.0 Hz, 1H), 7.31 (Br t, J=8.5 Hz, 1H), 7.60 (br d, J=6.0 Hz, 1H), 7.71 (Br s, 1H), 8.39 (br s, 1H), 8.67 (br s, 1H). MS: m/z 362 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07709645B2 |
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| Source dataset | uspto-grants-2010_05 |
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| ORD ID | ord-f07ef6a5c8f24ec999e17512110cb500 |
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| Source note | uspto-grants-2010_05 |
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