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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 74991Generated: October 29, 2026

Hydrochloric Acid → (1R,2S,6R)-2-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-6-methoxycyclohexanol

https://huagongshe.com/reaction/74991

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantLithium HydroxideHCID 3939—
ReactantSodium BicarbonateHCID 516892—
Reactant(1R,2S,6R)-2-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-6-methoxycyclohexanolHCID 68007375—
SolventTetrahydrofuranHCID 8028—
Product(1R,2S,6R)-2-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-6-methoxycyclohexanolHCID 6800821895.7%

Reaction Conditions

Temperature120 °C

Reaction Steps

In a microwave vial was placed azaindole 51k (0.050 g; 0.092 mmol). To this was added 3 mL of THF and 0.9 mL of 0.8 M LiOH. The vial was sealed and heated to 120° C. for 15 minutes in the microwave. When the reaction is complete, it was neutralized with 9 equivalents of 1N HCl (0.704 mL), then aqueous saturated NaHCO3 solution was added and the organic phase was separated and loaded onto silica gel for purification and eluted w/2% MeOH to 12% gradient over 10 minutes (4 g column) to provide 34.5 mg (91%) desired product 831.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08829007B2
Source datasetuspto-grants-2014_09
ORD IDord-28614521d66b4b0589f21e8b3e4fd728
Source noteuspto-grants-2014_09