HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylmorpholine → 3-(1-Methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid (1-cyclopropyl-piperidin-4-yl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733286 | — |
| Reactant | 1-Cyclopropylpiperidin-4-amine | HCID 16227644 | — |
| Reactant | 3-(1-Methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid | HCID 135961873 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(1-Methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid (1-cyclopropyl-piperidin-4-yl)-amide | HCID 135961816 | — |
Reaction Steps
100 mg of 3-(1-methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid is dissolved in 3 ml of dichloromethane and 139 mg of N-ethylmorpholine and 43.6 mg of TOTU (O-((ethoxycarbonyl)-cyanomehyleneamino)-N,N, N′,N′-tetramethyluroniumtetrafluoro) is added. After 5 minutes 34 mg of 1-cyclopropyl-piperidin-4-ylamine is added. The reaction is stirred for 48 h at RT. The product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 47 mg. LC-MS (ES+) 535 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07709466B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-cfdb77dbdec246028056d5888c22c08b |
| Source note | uspto-grants-2010_05 |