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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 629203Generated: October 30, 2026

Water → {(1S,2R)-2-[5-(3-Methyl-1H-indol-7-ylamino)-4-oxo-3,4-dihydro-pyrido[3,4-d]pyridazin-7-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/629203

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDiisopropylethylamineHCID 81531—
Reactant(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 1514389—
Reactant7-Chloro-5-((3-methyl-1H-indol-7-yl)amino)pyrido[3,4-d]pyridazin-4(3H)-oneHCID 89972411—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product{(1S,2R)-2-[5-(3-Methyl-1H-indol-7-ylamino)-4-oxo-3,4-dihydro-pyrido[3,4-d]pyridazin-7-ylamino]-cyclohexyl}-carbamic acid tert-butyl esterHCID 89972453—

Reaction Conditions

Temperature120 °C

Reaction Steps

To 7-chloro-5-(3-methyl-1H-indol-7-ylamino)-3H-pyrido[3,4-d]pyridazin-4-one (177 mg, 0.543 mmol) in NMP (1 ml) in a sealable glass vial, was added DIPEA (0.190 ml, 1.087 mmol) and tert-butyl(1S,2R)-2-aminocyclohexylcarbamate (233 mg, 1.087 mmol). The vial was capped to close and the reaction mixture was heated on a sandbath at 120° C. for 3 days. The resulting mixture was poured into water (20 ml), and extracted with EtOAc (20 ml). The organic phase was washed with water and brine, dried over Na2SO4, then concentrated under vacuum. The residue was triterated with DCM, then collected by filtration and dried to give a gummy solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09315500B2
Source datasetuspto-grants-2016_04
ORD IDord-feb174bf91304501956921b59a935653
Source noteuspto-grants-2016_04