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

HRID 507462

反応式

HRID 507462 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒3 回HCID 21226440Methylenechloride Hexane溶媒HCID 21584119Ethylacetate methanol溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-aaa9a787be5245399bc02482bc78573d
出典データセット
uspto-grants-2010_08
特許番号
US07786131B2

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