HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia methanol dichloromethane | HCID 21584172 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2(1H)-one | HCID 45786530 | — |
| Reactant | 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 | HCID 86703248 | — |
| Product | 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 | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365576B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-181feee139bd468fb04c87978d227e93 |
| Source note | uspto-grants-2016_06 |