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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 598504Generated: October 25, 2026

Hydrochloric Acid → [(R)-3-(6-Chloro-benzooxazol-2-ylamino)-pyrrolidin-1-yl]-o-tolyl-methanone

https://huagongshe.com/reaction/598504

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant2-Methylbenzoic acidHCID 8373—
ReactantDiisopropylethylamineHCID 81531—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant(6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-yl-amineHCID 57748894—
SolventDimethylformamideHCID 6228—
Product[(R)-3-(6-Chloro-benzooxazol-2-ylamino)-pyrrolidin-1-yl]-o-tolyl-methanoneHCID 5774896861.4%

Reaction Steps

A mixture of 32.9 mg (0.12 mmol) (6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-yl-amine; hydrochloride, 19.6 mg (0.144 mmol) 2-methyl-benzoic acid, 53.9 mg (0.168 mmol) TBTU and 77.5 mg (0.6 mmol) DIPEA in 2 mL DMF was stirred at room temperature for 16 h. The mixture was concentrated, taken up in methanol and formic acid and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 26.2 mg (61%) of the title compound. (MH+) 356.1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07897627B2
Source datasetuspto-grants-2011_03
ORD IDord-319c5c7a371c41038d972afcf6a6310f
Source noteuspto-grants-2011_03