HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-(2-((1S,2S)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (1S,2S)-2-Aminocyclohexanol hydrochloride | HCID 11715205 | — |
| Reactant | 2-Pyridinecarboxamide, N-methyl-4-[[2-(methylsulfinyl)-6-benzothiazolyl]oxy]- | HCID 57725393 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | 4-(2-((1S,2S)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide | HCID 57725464 | — |
Reaction Conditions
| Temperature | 110 °C |
|---|
Reaction Steps
To the solution of 4-(2-methanesulfinyl-benzothiazol-6-yloxy)-pyridine-2-carboxylic acid methylamide (70 mg, 0.202 mmol, 1.0 eq) in DMA (600 μL), was added (1S,2S)-2-aminocyclohexanol hydrochloride (92 mg, 0.606 mmol, 3.0 eq) followed by diisopropylethylamine (0.21 mL, 1.21 mmol). The reaction was heated at 110° C. for 24-hours. The neat reaction mixture was purified on reverse phase preparatory HPLC. Pure fractions were lyophilized as TFA salts. M+H=398
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07553854B2 |
| Source dataset | uspto-grants-2009_06 |
| ORD ID | ord-77096d7b94de438eab054f84383ec604 |
| Source note | uspto-grants-2009_06 |