HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-(6-Hydroxybenzothiazol-2-ylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Amino-6-benzothiazolol | HCID 33462 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid | HCID 392871 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(6-Hydroxybenzothiazol-2-ylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester | HCID 57980837 | 88.3% |
Reaction Steps
A solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (276 mg, 1.203 mmol), of HATU (549 mg, 1.444 mmol) and of diisopropylethylamine (187 mg, 1.44 mmol) in 3 ml of DMF is stirred at room temperature for 15 minutes. The 2-aminobenzothiazol-6-ol (intermediate 1) (200 mg, 1.203 mmol) dissolved in 3 ml of DMF is added in a single portion. The reaction medium is stirred at room temperature for 2 hours, poured into a 10% solution of Na2CO3 in water (20 ml) and extracted with ethyl acetate. The crude reaction product is purified by column chromatography (eluent: EtOAc/heptane (1/1)) to give 401 mg of 4-(6-hydroxybenzothiazol-2-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (white solid).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07632952B2 |
| Source dataset | uspto-grants-2009_12 |
| ORD ID | ord-616a751f903b45ab9fc3fbcbab4f00eb |
| Source note | uspto-grants-2009_12 |