HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-butyl 3-(4-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-5,6-dihydropyridin-1(2 H)-yl)azetidine-1-carboxylate formate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Oxo-azetidine-1-carboxylic acid tert-butyl ester | HCID 1519404 | — |
| Reactant | 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one formate | HCID 118131126 | — |
| Product | tert-butyl 3-(4-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-5,6-dihydropyridin-1(2 H)-yl)azetidine-1-carboxylate formate | HCID 118131307 | 19.3% |
Reaction Steps
Compound was prepared following the procedure described for the synthesis of Intermediate D24, from 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one formate (300 mg, 0.551 mmol) and tert-butyl 3-oxoazetidine-1-carboxylate (236 mg, 1.379 mmol), to afford tert-butyl 3-(4-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-5,6-dihydropyridin-1(2 H)-yl)azetidine-1-carboxylate formate (74.4 mg, 0.106 mmol, 19.30% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321776B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-174ec06f8cc44cbc913e80cf916ce318 |
| Source note | uspto-grants-2016_04 |