Potassium Carbonate → 1-{4-[4-(4-Tert-butyl-phenylamino)phenoxy]-6-methoxyquinolin-7-yloxy}-3-morpholin-4-ylpropan-2-ol

HRID 1727865노트

반응식

HRID 1727865 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:31]=[CH:30][C:15]([O:16][C:17]3[C:26]4[C:21](=[CH:22][C:23]([OH:29])=[C:24]([O:27][CH3:28])[CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(NC2C=CC(O[C:50]3[C:59]4[C:54](=CC(OCCCCl)=C(OC)C=4)[N:53]=[CH:52][CH:51]=3)=CC=2)=CC=1)(C)(C)C.C(=O)([O-])[O-:68].[K+].[K+].[CH2:73]([CH:75]1[O:77]C1)Br.C(OC(N1CCC(CO)CC1)=O)(C)(C)C>CN(C)C=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[CH:31]=[CH:30][C:15]([O:16][C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:29][CH2:50][CH:59]([OH:68])[CH2:54][N:53]5[CH2:52][CH2:51][O:77][CH2:75][CH2:73]5)=[C:24]([O:27][CH3:28])[CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 5

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate2회HCID 57567448(4-Tert-butylphenyl)-{4-[7-(3-chloropropoxy)-6-methoxy-4-quinolyloxy]phenyl}amineHCID 1357802514-[4-(4-Tert-butylphenylamino)phenoxy]-6-methoxyquinolin-7-ol2회

생성물 1

HCID 443820471-{4-[4-(4-Tert-butyl-phenylamino)phenoxy]-6-methoxyquinolin-7-yloxy}-3-morpholin-4-ylpropan-2-ol수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N,N-Dimethylformamide (2 ml) was added to 4-[4-(4-tert-butylphenylamino)phenoxy]-6-methoxyquinolin-7-ol (compound 21) (150 mg) (starting compound A) and potassium carbonate (250 mg). Epibromohydrin (46 μl) was added dropwise thereto, and the mixture was stirred at room temperature for 24 hr. Morpholine (95 μl) (starting compound B) was added dropwise to the reaction solution, and the mixture was stirred at 70 to 75° C. for 5 hr. The stirred mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and was dried over sodium sulfate. The solvent was then removed by evaporation under the reduced pressure. The crude thus obtained was purified by thin-layer chromatography on silica gel using chloroform/methanol for development to give the title compound (179 mg, yield 89%).

후처리

  1. stirringthe mixture was stirred at 70 to 75° C. for 5 hr
  2. extractionThe stirred mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialwas dried over sodium sulfate
  5. customThe solvent was then removed by evaporation under the reduced pressure
  6. customThe crude thus obtained
  7. customwas purified by thin-layer chromatography on silica gel

출처 및 근거

ORD 기록
ord-2fb71456f6874a8d853229cb485c66ff
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495104B2

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