HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloroacetamide → 2-(4-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloroacetamide | HCID 6580 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 90031541 | — |
| Reactant | 3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine | HCID 90064901 | — |
| Solvent | Acetone ethanol | HCID 21889777 | — |
| Product | 2-(4-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) acetamide | HCID 90031497 | 91.7% |
Reaction Steps
Using similar reaction conditions as described in step-i of example-82A, 3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step 2 compound of example 133) (100 mg, 0.16 mmol) was alkylated using 2-chloroacetamide (30 mg, 0.32 mmol), sodium bicarbonate (40 mg, 0.48 mmol) and ethanol/acetone (3/3 mL) to get 100 mg (91.7%) of the titled compound after purification by column (Silica gel 60/120) using 5% methanol in dichloromethane as eluent. MS: m/z=683.3 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-95063ae21a7f4516a0d498acbf8a64b8 |
| Source note | uspto-grants-2016_05 |