HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Isopropylhydrazine hydrochloride → 5-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-(4-chlorophenyl)-2-isopropyl-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(2H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Isopropylhydrazine hydrochloride | HCID 85573 | — |
| Reactant | 5-(3-acetyl-2-(4-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3-chloro-1-methyl-pyridin-2(1H)-one | HCID 117702763 | — |
| Product | 5-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-(4-chlorophenyl)-2-isopropyl-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(2H)-one | HCID 86292384 | — |
Reaction Steps
The title compound was prepared in analogy to the procedure described in Example 58 using 5-(3-acetyl-2-(4-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3-chloro-1-methyl-pyridin-2(1H)-one (Step 58.1) and isopropylhydrazine hydrochloride. The crude material was purified by preparative achiral SFC (column 4-Ethyl-pyridine, gradient 17-22% in 6 min_total 11 min). tR: 4.45 min (HPLC 1); tR: 1.01 min (LC-MS 2); ESI-MS: 431 [M+H]+ (LC-MS 2); Rf=0.31 (EtOAc); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34-1.42 (m, 6H) 2.07 (s, 3H) 3.43 (s, 3H) 4.52-4.62 (m, 1H) 6.12 (s, 1H) 7.23-7.30 (m, 2H) 7.34-7.40 (m, 2H) 7.87-7.90 (m, 1H) 7.90-7.93 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08975417B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-192b66cc695d42b38b910350400d7016 |
| Source note | uspto-grants-2015_03 |