HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| 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 | 4-Bromoquinoline-6-carboxylic acid | HCID 22388097 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide | HCID 118324067 | — |
Reaction Steps
To a mixture of 4-bromoquinoline-6-carboxylic acid (5 g), CH3ONH(CH3) hydrochloride salt (1.8 eq. 3.5 g), and HATU (1.15 eq. 8.67 g) in CH2Cl2 (100 mL) was slowly added triethylamine (4 eq. 11 mL) at 0° C. and the resulting reaction mixture was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 and water. The combined organics were washed with water several times, concentrated and then purified by chromatography (60-70% EtOAc/hexanes) to yield 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266835B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-b8d6dc208a804b06bc8dd84132d449ba |
| Source note | uspto-grants-2016_02 |