HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → tert-Butyl 4-[(4-{3-[[(4-chloro-1H-pyrrol-2-yl)carbonyl](2,4-dimethoxybenzyl)amino]prop-1-yn-1-yl}pyridin-2-yl)carbonyl]-1,4-diazepane-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-{5-[(7-Chloro-1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl}-1,4-diazepan-1-ium trifluoroacetate | HCID 68689209 | — |
| Reactant | 1-{[(4-Chloro-1H-pyrrol-2-yl)carbonyl]oxy}pyrrolidine-2,5-dione | HCID 86633423 | — |
| Reactant | tert-Butyl 4-[(4-{3-[(2,4-dimethoxybenzyl)amino]prop-1-yn-1-yl}pyridin-2-yl)carbonyl]-1,4-diazepane-1-carboxylate | HCID 86633427 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | tert-Butyl 4-[(4-{3-[[(4-chloro-1H-pyrrol-2-yl)carbonyl](2,4-dimethoxybenzyl)amino]prop-1-yn-1-yl}pyridin-2-yl)carbonyl]-1,4-diazepane-1-carboxylate | HCID 86633426 | — |
Reaction Steps
A solution of Example 6, F1 (2 eq), I2 (1 eq) and NaHCO3 (2.5 eq) in a mixture of CH3CN and H2O (20:1) was heated at reflux for 12 hrs and then the MeCN was removed under reduced pressure. The resulting residue was partitioned between DCM and water. The organic phase was washed with brine, dried (Na2SO4), filtered, concentrated under reduced pressure. The resulting brown oil was purified by Biotage system eluting with EtOAc/petroleum ether to obtain the desired compound. MS (ES) C33H38ClN5O6 requires: 635, found: 636 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07834015B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-219cd7cd2f2d4d2da9d32a35c67a3d64 |
| Source note | uspto-grants-2010_11 |