HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-(1-Isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid cyclopropylmethyl-propyl-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Cyclopropanemethanamine, N-propyl- | HCID 117787 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 5-(1-isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid | HCID 69282766 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-(1-Isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid cyclopropylmethyl-propyl-amide | HCID 69282888 | 37% |
Reaction Steps
A mixture of 0.07 mmol 5-(1-isopropyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid, 1.25 equiv. 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl uronium tetrafluoroborat, 1.25 equivalents cyclopropylmethyl-propyl-amine and 5 equivalents N-ethyldiisopropyl-amine in 0.7 ml DMF was stirred for 16 h at room temperature. The mixture was diluted with 0.8 ml methanol and subjected to preparative HPLC purification on reversed phase material eluting with a gradient of acetonitrile/water/triethyamine. The product fractions were evaporated to dryness to yield 9.1 mg (37%) of the title compound as light brown solid. MS (m/e): 384.5 (MH+, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07361682B2 |
| Source dataset | uspto-grants-2008_04 |
| ORD ID | ord-ac605805fa684fcfb9e44dd237ae607d |
| Source note | uspto-grants-2008_04 |