HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1778496Generated: November 2, 2026
Diisopropylethylamine → (1R,5S)-8-[[(4R)-4-(2-chloro-4-fluoro-phenyl)-5-methoxycarbonyl-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octane-5-carboxylic acid
https://huagongshe.com/reaction/1778496
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl (R)-6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate | HCID 89995948 | — |
| Reactant | HCID 117697565 | HCID 117697565 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (1R,5S)-8-[[(4R)-4-(2-chloro-4-fluoro-phenyl)-5-methoxycarbonyl-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]-3-oxa-8-azabicyclo[3.2.1]octane-5-carboxylic acid | HCID 117700395 | — |
Reaction Steps
A mixture of methyl (4R)-6-(bromomethyl)-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate (compound C, 61 mg, 0.138 mmol), 3-oxa-8-azabicyclo[3.2.1]octane-5-carboxylic acid 81a (20 mg, 0.127 mmol) and DIPEA (0.07 mL, 0.4 mmol) in DCM (5 mL) was stirred at 25° C. for 16 h. Then the mixture was concentrated in vacuo. The residue was purified by preparative HPLC to afford a pair of diastereomers, Example 81 and Example 82.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09266904B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-a64b12277a934718a1c91a9ec3b4e63b |
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| Source note | uspto-grants-2016_02 |
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