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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 587391Generated: October 30, 2026

Diisopropylethylamine → [(3S,4R)-4-(4-Chloro-phenyl)-1-(5'-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

https://huagongshe.com/reaction/587391

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant2-Bromo-5-(methylsulfonyl)pyridineHCID 9899483—
Reactant[(3S,4R)-4-(4-chloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl esterHCID 58303156—
SolventDimethylformamideHCID 6228—
Product[(3S,4R)-4-(4-Chloro-phenyl)-1-(5'-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl esterHCID 58303147—

Reaction Conditions

Temperature60 °C

Reaction Steps

A mixture of 20 mg (0.043 mmol) [(3S,4R)-4-(4-Chloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester, 11.2 uL (0.065 mmol) DIPEA and 12.8 mg (0.054 mmol) 2-bromo-5-(methylsulfonyl)pyridine in 1 mL DMF was heated to 60° C. over night. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions the title compound as light yellow viscous oil. MS m/e: 615.3 [M]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09226916B2
Source datasetuspto-grants-2016_01
ORD IDord-bcc7188aac904e41b6aedd7310dd69be
Source noteuspto-grants-2016_01