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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1898384Generated: October 31, 2026

Thionyl Chloride → HCID 178422800, compound

https://huagongshe.com/reaction/1898384

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
ReactantDiisopropylethylamineHCID 81531—
Reactant6-(Difluoromethoxy)pyridin-3-amineHCID 45090984—
ReactantHCID 178422815HCID 178422815—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178422800HCID 17842280014.5%

Reaction Steps

The title compound was prepared by following the procedure described for Example-108 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.100 g, 0.266 mmol), thionyl chloride (2.0 mL), 6-(difluoromethoxy)pyridin-3-amine (Intermediate-36, 0.065 g, 0.399 mmol), THF (5.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.020 g of the desired product. 1HNMR (DMSO-d6): δ 1.57 (s, 6H), 3.09 (s, 2H), 7.12 (d, J=8.7 Hz, 1H), 7.30-7.46 (m, 4H), 7.66 (s, 1H), 7.90 (s, 1H), 8.23 (d, J=9.0 Hz, 1H), 8.59 (s, 1H), 9.79 (s, 1H), 11.20 (s, 1H); MS [M+H]+: 518.24.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08519149B2
Source datasetuspto-grants-2013_08
ORD IDord-a99a5019070e48fdb5b293876dc6778a
Source noteuspto-grants-2013_08