HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → N2-(3-methoxypropyl)-N6-(tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroisoquinoline-2,6(1H)-dicarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3-Methoxypropylamine | HCID 1672 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | HCID 86656618 | HCID 86656618 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N2-(3-methoxypropyl)-N6-(tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroisoquinoline-2,6(1H)-dicarboxamide | HCID 86656594 | — |
Reaction Steps
A mixture of 0.074 ml 3-methoxyproylamine in 4 ml DMF is treated under an inert gas atmosphere is treated with 117 mg carbonyldiimidazole. After 2 h at ambient temperature the resulting mixture is treated with 200 mg of N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide and 10 mg DMAP. The reaction mixture is stirred overnight. After addition of 2 ml water the mixture is extracted twice with dichloromethane and the combined organic phases are dried and evaporated. The residue is purified by silica gel flash chromatography. 180 mg of yellowish oil are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08575193B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-68725e10fd44477f8b2b417d462a8f1b |
| Source note | uspto-grants-2013_11 |