2-Pyridinemethanamine → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitro-N-(2-pyridinylmethyl)-4-quinolinamine

HRID 1042987노트

반응식

HRID 1042987 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1>CC#N>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1

참가 물질

4

반응물 2

HCID 195092-PyridinemethanamineHCID 574655804-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole2회

생성물 1

HCID 672076287-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitro-N-(2-pyridinylmethyl)-4-quinolinamine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

A mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-3-nitroquinoline (for a preparation see Intermediate 18, 2.5 g, 7.5 mmol) and 2-aminomethylpyridine (2 eq, 1.41 g) in CH3CN (30 ml) was heated at 60° C. for 2 h. The mixture was extracted with DCM. The organic phase washed with saturated aqueous sodium hydrogen carbonate and dried over Na2SO4. The solvent was evaporated under reduced pressure and the residue taken up in diethyl ether. The precipitate was filtered off and dried in vacuo to give 7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-3-nitro-N-(2-pyridinylmethyl)-4-quinolinamine (2.5 g) which was used without purification in the next step.

후처리

  1. extractionThe mixture was extracted with DCM
  2. washThe organic phase washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationThe precipitate was filtered off
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-b74c366b94124301bb3995d39b06e5f5
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557984B2

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