참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hexane | HCID 8058 | — |
| 반응물 | Ethyl Acetate | HCID 8857 | — |
| 반응물 | 4-(Dimethylamino)butan-1-ol | HCID 83350 | — |
| 반응물 | N-(3-Bromophenyl)-7-fluoro-6-nitroquinazolin-4-amine | HCID 10761182 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 용매 | Methylenechloride Hexane | HCID 21226440 | — |
| 용매 | Ethylacetate methanol | HCID 21584119 | — |
| 생성물 | 6-amino-4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]quinazoline | HCID 10693912 | 33% |
반응 단계
To a suspension of hexane prewashed sodium hydride (11.0 mmol, 440 mg of a 60% dispersion in mineral oil) in THF (20 mL) was cannulated a solution of 4-(N,N-dimethylamino]butan-1-ol (8.80 mmol, 1.03 g) in THF (30 mL). The resulting suspension was stirred at 20° C. under N2 for 2 hours and then cannulated into a solution of 4-[(3-bromophenyl)amino]-7-fluoro-6-nitroquinazoline (J Med Chem, 1996;39:918-928) (0.80 g, 2.20 mmol) in THF (30 mL) under N2. The dark red solution was then heated at reflux overnight. Identical workup as above gave, after chromatography on grade III alumina eluting with EtOAc to MeOH/EtOAc (5:95) to give 6-amino-4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]quinazoline (310 mg, 33%) as a pale brown powder, mp (CH2Cl2/hexane) 155-156° C.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US06602863B1 |
|---|
| 출처 데이터셋 | uspto-grants-2003_08 |
|---|
| ORD ID | ord-1f296bc157464222b7282219bbb86873 |
|---|
| 출처 메모 | uspto-grants-2003_08 |
|---|
