(R)-1-Pyridin-2-yl-ethylamine → 7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-4-(((R)-1-(pyridin-2-yl)ethyl)amino)quinoline-3-carboxamide

HRID 1043008

반응식

HRID 1043008 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[C:21]([NH2:23])=[O:22].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C@H:30]([NH2:32])[CH3:31]>CC#N>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:32][C@@H:30]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=4)[CH3:31])=[C:3]([C:21]([NH2:23])=[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 1084918(R)-1-Pyridin-2-yl-ethylamineHCID 574655814-Chloro-7-(3,5-dimethylisoxazol-4-yl)-6-methoxyquinoline-3-carboxamide

생성물 1

HCID 574655857-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-4-(((R)-1-(pyridin-2-yl)ethyl)amino)quinoline-3-carboxamide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
110 °C

실험 절차

The mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-3-quinolinecarboxamide (for a preparation see intermediate 40, 6 g, 18 mmol) was reacted with (1R)-1-(2-pyridinyl)ethanamine (2 eq., 4.43 g, 36 mmol) in CH3CN (100 ml) and was stirred at 110° C. for 4 h. The reaction mixture was concentrated in vacuo. The residue was partitioned between water and DCM. The organic layer was dried over Na2SO4 and concentrated to dryness to give 7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-4-{[(1R)-1-(2-pyridinyl)ethyl]-amino}-3-quinolinecarboxamide which was used in the next step without purification. The carboxamide intermediate (6 g) was treated with an excess of [bis(trifluoroacetoxy)iodo]benzene (19.35 g, 45 mmol) in CH3CN (100 ml), the mixture was stirred at room temperature overnignt. The reaction mixture was concentrated in vacuo, the resulting residue was dissolved in DCM and washed with water. The crude product was purified by flash chromatography on silica gel (DCM/MeOH, 95:5), the resulting compound was dissolved in DCM and precipitated from diethylether to give the title compound as an off-white powder (2.5 g, 33%)

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between water and DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-f5f6cb51f27748e4acd5db71fa5aeda3
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557984B2

연결된 노트

불러오는 중…