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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204427Generated: November 1, 2026

Ammonia methanol dichloromethane → 5-(5-Chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one

https://huagongshe.com/reaction/2204427

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmonia methanol dichloromethaneHCID 21584172—
Reactant1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2(1H)-oneHCID 45786530—
Reactant2-bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-oneHCID 86703248—
Product5-(5-Chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-oneHCID 86703247—

Reaction Steps

The title compound was prepared in analogy to the procedure described in Example 240 but using 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one (Step 242.1) and 2-bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (Step 250.1). tR: 0.83 min (LC-MS 6); ESI-MS: 521.2/523.2 [M+H]+ (LC-MS 6); TLC (CH2Cl2/MeOH/NH3 94:5:1): Rf=0.18; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.35-0.450 (m, 1 H) 0.74-0.84 (m, 2 H) 1.12-1.25 (m, 1 H) 3.06-3.18 (m, 1 H) 3.41 (s, 3 H) 3.37 (s, 3 H) 6.30 (s, 1 H) 6.47 (dd, J=7.04, 1.95 Hz, 1 H) 6.52-6.61 (m, 1 H) 6.71 (s, 1 H) 7.30 (m, J=8.21 Hz, 2 H) 7.38 (m, J=8.60 Hz, 2 H) 7.62 (d, J=7.04 Hz, 1 H) 7.80-7.95 (m, 2 H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365576B2
Source datasetuspto-grants-2016_06
ORD IDord-181feee139bd468fb04c87978d227e93
Source noteuspto-grants-2016_06