HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxalyl chloride → 2-[4-(Tetrahydro-pyran-2-carbonyl)piperazinyl]-4-amino-6,7-dimethoxyquinazoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 1-Benzylpiperazine | HCID 75994 | — |
| Reactant | 2-Chloro-6,7-dimethoxy-4-quinazolinamine | HCID 90235 | — |
| Reactant | Oxane-2-carboxylic acid | HCID 10964532 | — |
| Reactant | N-benzyl-N'-(tetrahydropyran-2-carbonyl)piperazine | HCID 20310402 | — |
| Reactant | (Oxan-2-yl)(piperazin-1-yl)methanone | HCID 20385082 | — |
| Reactant | Sodium 3,4-dihydro-2H-pyran-2-carboxylate | HCID 23665163 | — |
| Product | 2-[4-(Tetrahydro-pyran-2-carbonyl)piperazinyl]-4-amino-6,7-dimethoxyquinazoline | HCID 20310400 | — |
Reaction Steps
To prepare the compound of formula III, the 3,4-dihydro-2H-pyran-2 carboxylic acid sodium salt is hydrogenated to the tetrahydro-pyran-2-carboxylic acid. This compound converted to the acid chloride with oxalyl chloride and is then treated with N-benzyl piperazine. The resultant N-benzyl-N'-(tetrahydropyran-2-carbonyl)piperazine is hydrogenated to giveN-(tetrahydro-pyran-2-carbonyl)piperazine. This compound is reacted with the known compound 4-amino-2-chloro-6,7-dimethoxyquinazoline to give the active drug 2-[ 4-(tetrahydro-pyran-2-carbonyl)piperazinyl]-4-amino-6,7-dimethoxyquinazoline.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04026894 |
| Source dataset | uspto-grants-1977_05 |
| ORD ID | ord-aa4a700664d14bbda07ece18d0d20a83 |
| Source note | uspto-grants-1977_05 |