Sodium Cyanide → 4-[(4-Methoxyphenyl)(methyl)amino]quinazoline-2-carbonitrile

HRID 1876152노트

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HRID 1876152 반응식
Cl.Cl[C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C-]#N.[Na+].[N:26]12CCN(CC1)C[CH2:27]2>CS(C)=O.CC(O)C.O.C(OCC)(=O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:13]([CH3:14])[C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=[C:3]([C:27]#[N:26])[N:12]=2)=[CH:16][CH:17]=1

참가 물질

8

반응물 3

HCID 8929Sodium CyanideHCID 9237DabcoHCID 86639964(2-Chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride

생성물 1

HCID 575165474-[(4-Methoxyphenyl)(methyl)amino]quinazoline-2-carbonitrile수율 139.4%

시약·촉매·용매 4

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

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온도
35 °C

실험 절차

To a solution of (2-chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride (56 mg, 0.17 mmol) in 1 mL of DMSO and 0.5 mL of 2-propanol were added sodium cyanide (16 mg, 0.34 mmol) and 1,4-diazabicyclo[2.2.2]octane (9 mg, 0.084 mmol). The mixture was heated at 35° C. for 1 d with stirring. The solution was diluted with 5 mL of water and 10 mL of ethyl acetate. The organic layer was washed with water, then dried and concentrated. The resulting crude material was purified by silica gel column chromatography to give the title compound (34 mg, 70%). 1H NMR (CDCl3, 400 MHz) δ 7.85 (d, 1H, J=8.4 Hz), 7.64 (t, 1H, J=6.8 Hz), 7.14 (m, 3H), 6.96 (m, 3H), 3.86 (s, 3H), 3.61 (s, 3H); ESI-MS m/z 291 (M+H)+.

후처리

  1. washThe organic layer was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe resulting crude material was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bfb59ba6a15e49e489559cf83a4456ce
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309562B2

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