Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Isovaleryl chloride | HCID 66054 | — |
| Reactant | HCID 58964283 | HCID 58964283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 11634087 | HCID 11634087 | 73% |
Reaction Steps
To a solution of 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)-4-(2-(3-methoxyazetidin-1-yl)ethoxy)benzenamine (40.3 mg, 0.107 mmol) and pyridine (35 μL) in CH2Cl2 (2 mL) was added isovaleryl chloride (15 μL, 0.122) and stirred for two hours. The resulting material was purified by HPLC. The product was dried in vacuo to afford the title compound as a white solid (36.0 mg, 73%). LCMS m/z (%)=465 (M+H 79Br, 75), 467 (M+H 81Br, 90). 1H NMR (400 MHz, DMSO-d6) δ: 10.00 (bs, 1H), 7.69 (dd, J=8.99, 2.65 Hz, 1H), 7.60 (s, 1H), 7.48 (d, J=2.63 Hz, 1H), 7.09 (d, J=9.06 Hz, 1H), 4.03-3.86 (m, 2H), 3.82 (quint, J=5.76 Hz, 1H), 3.65 (s, 3H), 3.35-3.28 (m, 1H), 3.24-3.17 (m, 1H), 3.08 (s, 3H), 2.73-2.55 (m, 41H), 2.16 (d, J=6.96 Hz, 2H), 2.12-2.00 (m, 1H), 0.92 (d, J=6.55 Hz, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07884101B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-092f7a6cf58f4e6396ea7932ae836f28 |
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| Source note | uspto-grants-2011_02 |
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