HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphosgene → 3-Isobutyl-N-(2-(4-methylpiperazin-1-yl)benzyl)-1-oxo-3-phenyl-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | 2-(4-Methyl-1-piperazinyl)benzenemethanamine | HCID 2795568 | — |
| Reactant | 3-cyclohexyl-3-isobutyl-N-((2-(4-methylpiperazin-1-yl)cyclohexyl)methyl)-1-oxo-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carboxamide | HCID 89615821 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 3-Isobutyl-N-(2-(4-methylpiperazin-1-yl)benzyl)-1-oxo-3-phenyl-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carboxamide | HCID 89615818 | — |
Reaction Steps
An analogous procedure to that described for R06039-275 was used to convert [2-(4-methylpiperazin-1-yl)phenyl]methanamine to 3-cyclohexyl-3-isobutyl-N-((2-(4-methylpiperazin-1-yl)cyclohexyl)methyl)-1-oxo-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carboxamide using triphosgene and triethylamine. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.82-0.90 (m, 3H), 0.90-1.00 (m, 3H), 1.58-1.73 (m, 1H), 1.74-1.88 (m, 1H), 2.25-2.46 (m, 3H), 2.34 (s, 3H), 2.49-2.67 (m, 4H), 2.98 (t, J=4.90 Hz, 4H), 3.23-3.38 (m, 1H), 3.55 (dt, J=13.56, 5.09 Hz, 1H), 3.93 (dt, J=19.21, 2.64 Hz, 1H), 4.43-4.59 (m, 3H), 6.05 (t, J=5.27 Hz, 1H), 7.02-7.19 (m, 2H), 7.22-7.43 (m, 7H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150582B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-11fee19ab2a948549727d29a4ce0fe21 |
| Source note | uspto-grants-2015_10 |