2-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanol → 2-{2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazoline-7-yloxy]-ethoxy}-ethanol

HRID 1255970

반응식

HRID 1255970 반응식
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16](F)=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[C:4]([F:24])[CH:3]=1.C([Si](C)(C)[O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36])(C)(C)C.C([Si](C)(C)OCCOC(O)C)(C)(C)C.C[Si](C)(C)[O-].[K+]>CS(C)=O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36])=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[C:4]([F:24])[CH:3]=1

참가 물질

6

반응물 4

HCID 111175822-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanolHCID 111761854-[(3,4-Dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline2회HCID 23668039Potassium trimethylsilanolateHCID 86618841HCID 86618841, 화합물

생성물 1

HCID 692669552-{2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazoline-7-yloxy]-ethoxy}-ethanol수율 24%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
25 °C

실험 절차

(4,5-Dichloro-2-fluoro-phenyl-(7-fluoro-6-nitro-quinazolin-4-yl)-amine (Compound 25, 0.723 grams, 1.94 mmol), 2-[2-(tert-butyl-dimethyl -silanyloxy)-ethoxy]-ethanol (Compound 28a (0.64 grams, 2.9 mmol) and potassium trimethylsilanolate (0.75 gram, 5.83 mmol) were dissolved in dry DMSO (42 ml) and the resulting mixture was stirred under nitrogen atmosphere for 5 hours at 25° C. The obtained deep crimson mixture was thereafter extracted with ethyl acetate (EtOAc) and water, and the organic phase was washed with NaHCO3 (4%) and brine, and dried over Na2SO4. The solvent was then removed under reduced pressure and the residue was purified by silica gel column chromatography, using a mixture of 2% MeOH in CH2Cl2 as eluent, to obtain Compound 29a (0.217 gram, 24% yield).

후처리

  1. extractionThe obtained deep crimson mixture was thereafter extracted with ethyl acetate (EtOAc) and water
  2. washthe organic phase was washed with NaHCO3 (4%) and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was then removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. additiona mixture of 2% MeOH in CH2Cl2 as eluent

출처 및 근거

ORD 기록
ord-82e84905b8024401aa14f0e858ee0c02
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461166B2

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