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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1685345Generated: November 1, 2026

Hydrochloric Acid → 4-(2-(5-((Tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acid

https://huagongshe.com/reaction/1685345

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantWaterHCID 962—
ReactantSodium HydroxideHCID 14798—
ReactantMethyl 4-(2-(5-((tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinateHCID 59200482—
SolventTetrahydrofuranHCID 8028—
Product4-(2-(5-((Tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acidHCID 5920040487%

Reaction Steps

A solution of methyl 4-(2-(5-((tert-butoxycarbonylamino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinate (1.28 g, 2.60 mmol) in tetrahydrofuran (40 mL) was treated with sodium hydroxide (5N, 3.12 mL, 15.6 mmol) at 23° C. The reaction was stirred for 2 hours, then acidified with conc. HCl to pH ˜2.0. Water was then added and the aqueous phase was extracted with ethyl acetate/THF. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (1.08 g, 87%) as a solid which was used as such in the next reaction.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08148400B2
Source datasetuspto-grants-2012_04
ORD IDord-f937941bd73b4ee3ae3f4db29985ab76
Source noteuspto-grants-2012_04