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

HRID 1876208노트

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HRID 1876208 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

{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]+)).

후처리

  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%)

출처 및 근거

ORD 기록
ord-4ab4549647c4437aa2ea116ff23414c1
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309562B2

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