HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-(2-(2-ethyl-6-fluorindoline-1-carbonyl)pyridin-4-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 4-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)picolinic acid | HCID 58117517 | — |
| Reactant | 2-ethyl-6-fluoro-2,3-dihydro-1H-indole | HCID 58117539 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-(2-(2-ethyl-6-fluorindoline-1-carbonyl)pyridin-4-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one | HCID 49801376 | — |
Reaction Steps
186 mg (0.50 mmol) 4-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)picolinic acid, 220 mg (0.60 mmol) 2-ethyl-6-fluoro-2,3-dihydro-1H-indole, 0.26 mL (1.5 mmol) DIPEA and 0.18 g (0.55 mmol) TBTU in 5.0 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and the organic solvent was evaporated down. The aqueous residue was made alkaline with 1N aqueous sodium hydroxide solution, the precipitate formed was suction filtered, washed with water and dried under HV.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08110575B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-a643f4faeee54105abbaf11f5eaed78d |
| Source note | uspto-grants-2012_02 |