Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | HCID 86681456 | HCID 86681456 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86681457 | HCID 86681457 | 36.5% |
Reaction Steps
A solution of 2-[(2S)-2-[5-(4-fluoro-1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione (30.0 mg, 0.058 mmol) and hydrazine (0.2 mL, 6 mmol) in methanol (1.0 mL) and tetrahydrofuran (1.0 mL) was stirred at room temperature overnight. Direct purification on prep.—HPLC (pH=10) gave 8.1 mg of the desired product as white solid. LC/MS found: 383.0 (M+1)+; 1H NMR (400 MHz, DMSO-d6) δ ppm: 7.73 (d, J=7.8 Hz, 1H), 7.71 (s, 1H), 7.61 (d, J=4.9 Hz, 1H), 7.57 (d, J=7.9 Hz, 1H), 7.23 (ddd, J1=8.2 Hz, J2=7.8 Hz, J3=6.4 Hz, 1H), 7.03 (m, 2H), 6.93 (dddd, J1=8.6 Hz, J2=8.4 Hz, J3=2.6 Hz, J4=0.8 Hz, 1H), 4.48 (s, 2H), 4.42 (m, 1H), 3.79 (s, 3H), 3.05 (dd, J1=14.40 Hz, J2=5.20 Hz, 1H), 2.88 (dd, J1=14.40 Hz, J2=10.00 Hz, 1H), 2.81 (d, J=6.70 Hz, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08895571B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-470ab0e1e6784c669902fd47ce94f331 |
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| Source note | uspto-grants-2014_11 |
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