HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-(3-Oxa-8-azabicyclo[3.2.1]octan-6-yl)acetic acid → 2-[(1R,5S,6S)-8-[[(4R)-4-(2-bromo-4-fluoro-phenyl)-5-methoxycarbonyl-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octan-6-yl]acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-(3-Oxa-8-azabicyclo[3.2.1]octan-6-yl)acetic acid | HCID 117697829 | — |
| Reactant | (R)-methyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate | HCID 117706695 | — |
| Product | 2-[(1R,5S,6S)-8-[[(4R)-4-(2-bromo-4-fluoro-phenyl)-5-methoxycarbonyl-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octan-6-yl]acetic acid | HCID 117700220 | 24.2% |
Reaction Steps
The title compound was prepared in analogy to compound 1a in Example 1 starting from methyl (4R)-4-(2-bromo-4-fluoro-phenyl)-6-(bromomethyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate 53a (73 mg, 0.15 mmol) and 2-(3-oxa-8-azabicyclo[3.2.1]octan-6-yl)acetic acid (121 mg, 0.7 mmol) 64c. 21 mg of the title compound was isolated by preparative HPLC as a yellow powder (yield was 16%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266904B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-78e9458b48c8456087cec19c1121bf04 |
| Source note | uspto-grants-2016_02 |