HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → 6-benzyloxy-2-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-7-carboxylic acid [3-(4-fluoro-phenyl)-2-oxo-propyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 2-Propanone, 1-amino-3-(4-fluorophenyl)-, hydrochloride (1:1) | HCID 13290674 | — |
| Reactant | 6-benzyloxy-2-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-7-carboxylic acid | HCID 58514457 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-benzyloxy-2-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-7-carboxylic acid [3-(4-fluoro-phenyl)-2-oxo-propyl]-amide | HCID 67005205 | — |
Reaction Steps
To a solution of the product of example 1 (2.4 mmol) in THF (10 ml) was added compound 1-amino-3-(4-fluoro-phenyl)-propan-2-one hydrochloride (1.0 g, 4.9 mmol), EDCI.HCl (560 mg, 2.9 mmol), HOBt (400 mg, 2.9 mmol) and TEA (1 g, 9.9 mmol), successively at room temperature. The mixture was stirred overnight, after which saturated sodium bicarbonate was added and then extracted with ethyl acetate. The extracts were combined, washed with brine, and then dried over sodium sulfate. The product was purified by column chromatography to give the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08426405B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-3226fc47e52e4e29a53985d1a949dfc2 |
| Source note | uspto-grants-2013_04 |