HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 5-Cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid | HCID 71087254 | — |
| Reactant | 5-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid | HCID 71087560 | — |
| Reactant | (S)-2-Cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine | HCID 86674748 | — |
| Reactant | Cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methylamine | HCID 86674778 | — |
| Product | 5-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-amide | HCID 71105651 | — |
Reaction Steps
In analogy to the procedure described in Example 47 b), 5-cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid (which can e.g. be prepared in a similar manner than 5-cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid (Example 4 b)) was reacted with cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methylamine (which can e.g. be prepared in a similar manner than (S)-2-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (Example 32 e)) in the presence of TBTU and DIEA to obtain the title compound as colorless oil; MS (EI): m/e=413.1 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09303012B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-abe02f64ebdf484da8a4e98f636653d9 |
| Source note | uspto-grants-2016_04 |