HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-Chloro-N-methyl-6-isoquinolinecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | 3-Chloroisoquinoline-6-carboxylic acid | HCID 75412036 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-Chloro-N-methyl-6-isoquinolinecarboxamide | HCID 89995629 | 61% |
Reaction Steps
HATU (17.6 mg, 0.046 mmol) was added to a solution of 3-chloroisoquinoline-6-carboxylic acid (Preparation 54, 8 mg, 0.039 mmol), DIPEA (54 uL, 0.31 mmol) and methanamine hydrochloride (15.6 mg, 0.231 mmol) in DMF (4 mL) and the reaction was stirred for 18 hours. The reaction was partitioned between EtOAc and brine, the separated organic phase was washed with saturated NaHCO3 solution, citric acid and brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound as yellow oil (5.2 mg, 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09334286B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-0ade811839ac4f67b956930f55d3869d |
| Source note | uspto-grants-2016_05 |