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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1265927Generated: November 2, 2026

4-Pyridylthiourea → 8-Chloro-7-dimethylamino-4-{3-[2-(pyridin-4-ylamino)-thiazol-4-yl]-phenyl}-1,3-dihydro-benzo[b][1,4]diazepin-2-one

https://huagongshe.com/reaction/1265927

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-PyridylthioureaHCID 2737249—
Reactant4-(3-Bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-oneHCID 18613234—
SolventTetrahydrofuranHCID 8028—
SolventEthyl AcetateHCID 8857—
Product8-Chloro-7-dimethylamino-4-{3-[2-(pyridin-4-ylamino)-thiazol-4-yl]-phenyl}-1,3-dihydro-benzo[b][1,4]diazepin-2-oneHCID 1861350237.6%

Reaction Conditions

Temperature60 °C

Reaction Steps

A mixture of 4-(3-bromoacetyl-phenyl)-8-chloro-7-dimethylamino-1,3-dihydro-benzo[b][1,4]diazepin-2-one (130 mg) (Example 193a) and 1-(4-pyridyl)-2-thiourea (46 mg) in THF (3 mL) was heated at 60° C. for 45 min. The mixture was diluted with AcOEt and washed with sat. NaHCO3 solution and with brine. The organic layer was dried and evaporated and the residue was triturated with Et2O to give the title compound (55 mg) as yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06544985B2
Source datasetuspto-grants-2003_04
ORD IDord-38e8eed7f22c4f33860e1d31f22fa009
Source noteuspto-grants-2003_04