HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acrylic Acid → N-[4-(3-Bromo-phenylamino)-7-(4-dimethylamino-butoxy)-quinazolin-6-yl]-acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acrylic Acid | HCID 6581 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 6-amino-4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]quinazoline | HCID 10693912 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Solvent | Ethylacetate methanol | HCID 21584119 | — |
| Solvent | Ethyl ether methylene chloride | HCID 21881112 | — |
| Product | N-[4-(3-Bromo-phenylamino)-7-(4-dimethylamino-butoxy)-quinazolin-6-yl]-acrylamide | HCID 10600888 | 32% |
Reaction Steps
To a stirred solution of the above 6-aminoquinazoline (276 mg, 0.64 mmol), acrylic acid (6 mol eq., 3.85 mmol, 264 mL), and Et3N (excess, 1.0 mL) in DMA (10 mL) under N2 was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl) (3 mol eq., 1.92 mmol, 369 mg). The standard procedure above was followed to give after chromatography on grade III alumina eluting with EtOAc/hexane (1:1) to MeOH/EtOAc (3:97), N-[4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]-quinazolin-6-yl]acrylamide (98 mg, 32%) as a cream powder, mp (CH2Cl2/Et2O) 112-115° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07786131B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-3e68c912f14d41b1822ac71bd63da872 |
| Source note | uspto-grants-2010_08 |