Dimethylformamide → 2-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-yl}-2-methyl-propionitrile

HRID 1876208ノート

反応式

HRID 1876208 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7]C(CNC2C3C(=CC=CC=3)N=C(CC#N)N=2)=[CH:5][CH:4]=1.Cl.ClCC1[N:36]=[C:35]([N:37]([C:39]2[CH:44]=[CH:43][C:42](OC)=[CH:41][CH:40]=2)C)[C:34]2[C:29](=CC=C[CH:33]=2)[N:28]=1.[C:47]([O-])([O-])=O.[Na+].[Na+].[C-]#N.[Na+].[CH3:56][N:57]([CH:59]=O)[CH3:58]>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:59]([N:57]([CH3:56])[C:58]2[C:40]3[C:39](=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:37]=[C:35]([C:34]([CH3:33])([CH3:47])[C:29]#[N:28])[N:36]=2)=[CH:5][CH:4]=1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 10340Sodium CarbonateHCID 68515345HCID 68515345、化合物HCID 68517170{4-[(4-Methoxyphenyl)methylamino]-quinazolin-2-yl}acetonitrile

生成物 1

HCID 592420352-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-yl}-2-methyl-propionitrile収率 36%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

{4-[(4-Methoxyphenyl)methylamino]-quinazolin-2-yl}acetonitrile: A suspension of (2-chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine hydrochloride (985 mg, 2.8 mmol), Na2CO3 (465 mg, 4.4 mmol) and NaCN (151 mg, 3.1 mmol) in DMF (10 mL) was stirred at 70° C. overnight. The reaction was cooled to rt, diluted with EtOAc and washed with H2O. The organics were dried (MgSO4), filtered, concentrated and purified by gradient MPLC (SiO2, EtOAc/hexanes, 0-100%) to provide 310 mg (36%) of the title compound. 1H NMR (CDCl3) δ 7.75 (d, 1H), 7.57 (ddd, 1H), 7.17-7.11 (m, 2H), 7.06-6.91 (m, 4H), 4.05 (s, 2H), 3.86 (s, 3H), 3.63 (s, 3H); LC-MS (ESI+; 305 ([M+H]+)).

後処理

  1. temperatureThe reaction was cooled to rt
  2. washwashed with H2O
  3. dry with materialThe organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by gradient MPLC (SiO2, EtOAc/hexanes, 0-100%)

出典と根拠

ORDレコード
ord-4ab4549647c4437aa2ea116ff23414c1
出典データセット
uspto-grants-2012_11
特許番号
US08309562B2

反応ノート

読み込み中…