Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Reactant | 4-[3,4-Diamino-2-(2,4-difluorophenoxy)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one | HCID 118093828 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178427325 | HCID 178427325 | 79% |
Reaction Steps
A solution of 4-[3,4-diamino-2-(2,4-difluorophenoxyl)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (0.040 g, 0.074 mmol) in acetic acid (0.1 mL, 3 mmol) was treated with water (0.37 mL, 21 mmol) followed by sodium nitrite (0.026 g, 0.37 mmol) and stirred at 20° C. for 30 min. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate (2×) and brine, dried with magnesium sulfate, filtered, and concentrated to give the desired product (32 mg, 78%) as a crude brown residue that was used immediately without further purification. LCMS calculated for C27H20F2N5O4S (M+H)+: m/z=548.1. found: 548.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09399640B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-17cb995d487c4b40ab1a756274369c3b |
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| Source note | uspto-grants-2016_07 |
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