Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyruvic Acid | HCID 1060 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 86693909 | HCID 86693909 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57344126 | HCID 57344126 | 46.4% |
Reaction Steps
4-(3-(1,4-diazepane-1-carbonyl)-4-fluorobenzyl)phthalazin-1(2H)-one TFA salt (320 mg, 0.65 mmol), 2-oxopropanoic acid [0.3 ml (d=1.26), 4.29 mmol], DIPEA (1 ml, 6 mmol), and HATU (510 mg, 1.34 mmol) were mixed in DMF (30 ml). After the resulting reaction mixture was stirred at room temperature for 60 h, the reaction mixture was partition between DCM and water (100 ml each). The aqueous phase was extracted with DCM (100 ml), and the combined organic phase was washed with water, sat. aqueous sodium bicarbonate, and brine, dried over sodium sulphate, filtered, and concentrated to yield the crude product. Then the crude product was purified by column chromatography on silica gel (Petroleum ether:Ethyl Acetate=1:2) to afford the desired product (136 mg, 45.1%) as an off white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08999985B2 |
|---|
| Source dataset | uspto-grants-2015_04 |
|---|
| ORD ID | ord-e25869ef2d8c4e80b4c35e7f6c03a2ab |
|---|
| Source note | uspto-grants-2015_04 |
|---|
