HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 2-(2-Oxo-3-pyridin-2-ylimidazolidin-1-yl)-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-oxo-3-(2-pyridinyl)-1-Imidazolidineacetic acid | HCID 18442642 | — |
| Reactant | 5-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one | HCID 59166722 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(2-Oxo-3-pyridin-2-ylimidazolidin-1-yl)-N-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)acetamide | HCID 11626635 | — |
Reaction Steps
A mixture of (2-oxo-3-pyridin-2-ylimidazolidin-1-yl)acetic acid (22 mg, 0.10 mmol, described in Intermediate 14), (−)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (25 mg, 0.10 mmol, described in Intermediate 4), EDC (19 mg, 0.10 mmol), HOBT (15 mg, 0.10 mmol), and N,N-diisopropylethylamine (0.0138 mL, 0.10 mmol) is stirred in DMF (0.5 mL) at ambient temperature for 18 h. The crude mixture is purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H-90:10:0.1 to 5:95:0.1. Lyophilization provides the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07659300B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-74ccc18e77a14d2c9434817a6ae145a9 |
| Source note | uspto-grants-2010_02 |