Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cyclobutylamine | HCID 75645 | — |
| 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-(7-hydroxy-1-oxo-1H-isoquinolin-2-yl)-4-methylbenzoic acid | HCID 67018587 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 11624421 | HCID 11624421 | 43.1% |
Reaction Steps
3-(7-Hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (295 mg), HATU (406 mg) and cyclobutylamine (0.43 ml) were dissolved in DMF (25 ml) and stirred at room temperature for 18 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (magnesium sulfate) and concentrated. The residue was purified by column chromatography with ethyl acetate to give N-cyclobutyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as a white solid (150 mg); NMR Spectrum: (DMSOd6) 1.35 (m, 2H), 2.03 (m, 2H), 2.10 (s, 3H), 2.20 (m, 2H), 4.40 (m, 1H), 6.65 (d, 1H), 7.12 (d, 1H), 7.22 (m, 1H), 7.46 (d, 1H), 7.60 (m, 2H), 7.76 (s, 1H), 7.85 (d, 1H) 8.60 (d, 1H), 10.00 (s, 1H); Mass Spectrum: M+H+ 349.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07786115B2 |
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| Source dataset | uspto-grants-2010_08 |
|---|
| ORD ID | ord-d2a9190bf61e47229e00cf6c36eea066 |
|---|
| Source note | uspto-grants-2010_08 |
|---|
