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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1426913Generated: October 30, 2026

Cesium carbonate → (6R)-9-fluoro-15-hydroxy-13-oxa-2,11,17,21,22,25-hexazapentacyclo[17.5.2.02,6.07,12.022,26]hexacosa-1(25),7(12),8,10,19(26),20,23-heptaen-18-one

https://huagongshe.com/reaction/1426913

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantN-(3-chloro-2-hydroxypropyl)-5-((R)-2-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamideHCID 67471084—
SolventDimethylformamideHCID 6228—
Product(6R)-9-fluoro-15-hydroxy-13-oxa-2,11,17,21,22,25-hexazapentacyclo[17.5.2.02,6.07,12.022,26]hexacosa-1(25),7(12),8,10,19(26),20,23-heptaen-18-oneHCID 70167830—

Reaction Conditions

Temperature85 °C

Reaction Steps

A suspension of N-(3-chloro-2-hydroxypropyl)-5-((R)-2-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (100 mg, 0.23 mmol) and Cs2CO3 (375 mg, 1.15 mmol) in DMF (3 mL) was heated at 85° C. for 2 hours. The reaction mixture was filtered through a GF/F paper and directly purified on reverse phase column chromatography (Biotage SP4 system C-18 25+M column, 5 to 50% acetonitrile/water), to provide the title product as a white solid. MS (apci) m/z=399.2 (M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08933084B2
Source datasetuspto-grants-2015_01
ORD IDord-bb65af795d104beea3b0c81777db3d7c
Source noteuspto-grants-2015_01