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

反応式

HRID 1255970 の反応式
[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

参加物

6

反応物 4

HCID 111175822-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanolHCID 111761854-[(3,4-Dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline2 回HCID 23668039Potassium trimethylsilanolateHCID 86618841HCID 86618841、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
25 °C

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-82e84905b8024401aa14f0e858ee0c02
出典データセット
uspto-grants-2013_06
特許番号
US08461166B2

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