HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → tert-butyl 3-(3-((4-methoxy-6-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-ylamino)methyl)phenoxy)propylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | tert-butyl N-(3-hydroxypropyl)carbamate | HCID 3838134 | — |
| Reactant | 3-((4-methoxy-6-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-ylamino)methyl)phenol | HCID 67439819 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-butyl 3-(3-((4-methoxy-6-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-ylamino)methyl)phenoxy)propylcarbamate | HCID 67440753 | — |
Reaction Steps
To a mixture of Example 63A (0.510 g, 1.05 mmol), tert-butyl 3-hydroxypropylcarbamate (0.275 g, 1.57 mmol) and triphenylphosphine (0.412 g, 1.57 mmol) in tetrahydrofuran (13 ml) was added dropwise diisopropyl azodicarboxylate (DIAD) (0.305 ml, 1.57 mmol). The reaction mixture was stirred at room temperature for 3 hours and then concentrated in vacuo. Flash chromatography isolation (gradient elution, ethyl acetate/hexane 0-50%) gave the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822446B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-d0580ac7dd1f407bac665877e171e160 |
| Source note | uspto-grants-2014_09 |