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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 60332Generated: October 30, 2026

Triethylamine → 5-[1-(2-Hydroxyethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

https://huagongshe.com/reaction/60332

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantHCID 67248027HCID 67248027—
SolventMethanolHCID 887—
Product5-[1-(2-Hydroxyethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileHCID 5325153045.6%

Reaction Steps

A solution of 9-benzenesulfonyl-5-[1-(2-hydroxyethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (125 mg, 0.26 mmol) and triethylamine (1 mL) in methanol (10 mL) was heated to 60° C. for 3 hours. The mixture was concentrated in-vacuo and the resultant residue purified by flash chromatography (silica, 10 g column, ISCO, 0-8% methanol in dichloromethane). The resultant material was triturated with acetonitrile and methanol to afford the title compound as an off-white solid (40 mg, 45%). LCMS (Method C): RT=4.83 min, M+H+=338.2. 1H NMR (400 MHz, DMSO-d6): 8.79 (s, 1H), 8.70 (dd, J=4.8, 1.6 Hz, 1H), 8.59 (dd, J=7.9, 1.7 Hz, 1H), 7.47 (dd, J=7.9, 4.8 Hz, 1H), 4.71-4.69 (m, 1H), 4.38 (s, 1H), 3.49 (s, 2H), 2.93-2.81 (m, 2H), 2.40 (t, J=6.3 Hz, 2H), 2.15 (t, J=11.1 Hz, 2H), 2.06 (d, J=12.0 Hz, 2H), 1.93-1.92 (m, 2H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440976B2
Source datasetuspto-grants-2016_09
ORD IDord-45c786810f0d45589df66848202b9e64
Source noteuspto-grants-2016_09