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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2182042Generated: November 2, 2026

Triethylamine → N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-(5-fluoro-2-pyridinyl)urea

https://huagongshe.com/reaction/2182042

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantP,P-Diphenylphosphinic azideHCID 199401—
Reactant2-Amino-5-fluoropyridineHCID 2737701—
Reactant(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acidHCID 21304923—
SolventTolueneHCID 1140—
ProductN-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-(5-fluoro-2-pyridinyl)ureaHCID 60077565—

Reaction Conditions

Temperature110 °C

Reaction Steps

(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid (50 mg, 0.22 mmol, ee ˜90%) was mixed with toluene (1 ml), triethylamine (0.034 ml, 1.1 eq), 2-amino-5-fluoropyridine (28 mg, 1.1 eq), DPPA (0.054 ml, 1.1 eq). The reaction mixture was then heated at stirring at 110° C. for 3 h. The reaction mixture was concentrated by rotary evaporation and purified by column chromatography on silica (50 g, ethylacetate/hexane 1:1) to give 30 mg of the product as white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06894177B2
Source datasetuspto-grants-2005_05
ORD IDord-76fa906743dc4f65b0d9cba42593e7ec
Source noteuspto-grants-2005_05