Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methylamine hydrochloride | HCID 6364545 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 67440493 | HCID 67440493 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67442038 | HCID 67442038 | 94.4% |
Reaction Steps
2-[3-(1-carboxy-1-methyl-ethylamino)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (410 mg, 1 mmol), methylamine hydrochloride (203 mg, 3 mmol) and o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (570 mg, 1.5 mmol) in dichloromethane (5 mL) and triethyl-amine (0.5 mL, 3 mmol) was stirred at 25° C. for 12 h. Then the reaction mixture was extracted with dichloromethane (2×100 mL), washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3,3-dimethyl-2-[3-(1-methyl-1-methylcarbamoyl-ethylamino)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (0.4 g, 94%) as a brown oil which was used for next step without further purification: LC/MS m/e calcd for C25H33N3O3 (M+H)+: 424.56, observed: 424.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08344137B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-4dde29ecc72b4fcea3aff0fe9b609561 |
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| Source note | uspto-grants-2013_01 |
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