HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-(6-(2,3-dihydro-1H-pyrrolo[3,2-c]pyridin-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydro-spiro[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 | 1H,2H,3H-pyrrolo(3,2-c)pyridine | HCID 12490979 | — |
| Reactant | 6-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl-amino)pyrimidine-4-carboxylic acid-hydrochloride | HCID 66722185 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-(6-(2,3-dihydro-1H-pyrrolo[3,2-c]pyridin-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydro-spiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one | HCID 49801090 | — |
Reaction Steps
0.15 g (0.37 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 45 mg (0.38 mmol) 2,3-dihydro-1H-pyrrolo[3,2-c]pyridine, 0.15 mL (0.87 mmol) DIPEA and 0.13 g (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. Then the reaction mixture was mixed with water, the precipitate formed was suction filtered and dissolved in DMF/NMP. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised. A second purification was carried out by preparative HPLC-MS.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08110575B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-cf910c5585fb4fffa7cd1487b996d1c5 |
| Source note | uspto-grants-2012_02 |