Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 118080513 | HCID 118080513 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 118080523 | HCID 118080523 | 73.2% |
Reaction Steps
Pyridine (4.07 μL, 0.050 mmol) was added to a solution of isopropyl (S)-4-acetyl-6-amino-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.010 g, 0.025 mmol) in 1,4-dioxane (200 μL). Methanesulfonyl chloride (1.96 μL, 0.025 mmol) was added, and the mixture stirred at rt for 18 h. The reaction mixture was concentrated and ethyl acetate was added. The solution was washed with 1 N aqueous HCl, and the organic phase was separated and concentrated to afford isopropyl (S)-4-acetyl-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-6-(methylsulfonamido)-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.0087 g, 73% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.07-1.16 (m, 6 H), 1.18-1.36 (m, 8H), 2.30 (s, 3 H), 2.99 (s, 3 H), 3.58-3.80 (m, 2 H), 3.84-3.99 (m, 1 H), 4.99-5.08 (m, 1 H), 6.85 (br s, 1 H), 7.49-7.50 (m, 1 H), 7.71 (d, J=4.40 Hz, 2 H), 7.97 (br s, 1 H). MS (ESI, pos. ion) m/z 476 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09422281B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-973da7493e554ddcb0618af7487a2e22 |
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| Source note | uspto-grants-2016_08 |
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