Hexane → 6-amino-4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]quinazoline

HRID 394739

반응식

HRID 394739 반응식
CCCCCC.[CH3:7][N:8]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH3:9].[Br:15][C:16]1[CH:17]=[C:18]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29](F)=[C:30]([N+:33]([O-])=O)[CH:31]=3)[N:26]=[CH:25][N:24]=2)[CH:19]=[CH:20][CH:21]=1.CCOC(C)=O>C1COCC1.C(Cl)Cl.CCCCCC.CO.CCOC(C)=O>[NH2:33][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][C:29]=1[O:14][CH2:13][CH2:12][CH2:11][CH2:10][N:8]([CH3:9])[CH3:7])[N:26]=[CH:25][N:24]=[C:23]2[NH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([Br:15])[CH:17]=1

참가 물질

8

반응물 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 833504-(Dimethylamino)butan-1-olHCID 10761182N-(3-Bromophenyl)-7-fluoro-6-nitroquinazolin-4-amine

생성물 1

HCID 106939126-amino-4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]quinazoline수율 33%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매3회HCID 21226440Methylenechloride Hexane용매HCID 21584119Ethylacetate methanol용매

반응 조건

온도
20 °C

실험 절차

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.

후처리

  1. temperatureThe dark red solution was then heated
  2. temperatureat reflux overnight
  3. customIdentical workup as above gave

출처 및 근거

ORD 기록
ord-1f296bc157464222b7282219bbb86873
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602863B1

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