Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Reactant | (S)-methyl 2-(3,4-diaminophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate | HCID 70664863 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 178497313 | HCID 178497313 | 21.1% |
Reaction Steps
To a solution of (S)-methyl 2-(3,4-diaminophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (600 mg, crude) in HCl (60 mL, 2N) was added sodium nitrite (164.7 mg, 2.39 mmol) in water (1 mL) dropwise at 0-5° C. The resulting solution was stirred for 15 min at 0° C., then diluted with water (150 mL), extracted with dichloromethane (3×80 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified via silica gel chromatography (1.25% methanol in dichloromethane) to afford (S)-methyl 2-(1H-benzo[d][1,2,3]triazol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (130 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08912188B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-774e96a2a1e646cabcd170a2e068ac3f |
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| Source note | uspto-grants-2014_12 |
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