Dimethylformamide → 3-methoxymethoxy-2,2-dimethylpropionic acid 5-{[4-(amino[benzoylimino]methyl)phenylamino]-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester

HRID 2089625

反応式

HRID 2089625 の反応式
[NH2:1][C:2](=[N:36][C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH2:32][CH2:33][OH:34])[C:24]=2[F:35])[C:11]2[NH:15][C:14](=[O:16])[N:13]([C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:12]=2)=[CH:5][CH:4]=1.CN(C=O)C.C(=O)([O-])O.[K+].Cl[CH2:56][O:57][C:58](=[O:67])[C:59]([CH3:66])([CH3:65])[CH2:60][O:61][CH2:62][O:63][CH3:64]>C(OCC)(=O)C>[NH2:1][C:2](=[N:36][C:37](=[O:44])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH2:32][CH2:33][OH:34])[C:24]=2[F:35])[C:11]2[N:15]=[C:14]([O:16][CH2:56][O:57][C:58](=[O:67])[C:59]([CH3:65])([CH3:66])[CH2:60][O:61][CH2:62][O:63][CH3:64])[N:13]([C:17]3[N:18]=[CH:19][CH:20]=[CH:21][N:22]=3)[N:12]=2)=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 516893Potassium BicarbonateHCID 866773923-Methoxymethoxy-2,2-dimethylpropionic acid chloromethyl esterHCID 136334022N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide

生成物 1

HCID 674704683-methoxymethoxy-2,2-dimethylpropionic acid 5-{[4-(amino[benzoylimino]methyl)phenylamino]-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester収率 25.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a mixture of N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide (120 mg) and DMF (3 mL), potassium hydrogen carbonate (30 mg) and 3-methoxymethoxy-2,2-dimethylpropionic acid chloromethyl ester (54.8 mg) were sequentially added, and the resulting mixture was stirred at 60° C. for 14 hours. To the mixture, ethyl acetate (100 mL) was added. The resulting mixture was sequentially washed three times with water (50 mL) and with saturated aqueous sodium chloride solution (50 mL), and dried over anhydrous magnesium sulfate. The resulting mixture was filtered and the obtained filtrate was concentrated under reduced pressure. The obtained residue was purified by NAM silica gel column chromatography (mixed solvent of heptane-ethyl acetate and methanol-ethyl acetate) to obtain the captioned compound (40 mg).

後処理

  1. additionwere sequentially added
  2. washThe resulting mixture was sequentially washed three times with water (50 mL)
  3. dry with materialwith saturated aqueous sodium chloride solution (50 mL), and dried over anhydrous magnesium sulfate
  4. filtrationThe resulting mixture was filtered
  5. concentrationthe obtained filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by NAM silica gel column chromatography (mixed solvent of heptane-ethyl acetate and methanol-ethyl acetate)

出典と根拠

ORDレコード
ord-b203e0a95e36404aa9a5fe0fcf105b38
出典データセット
uspto-grants-2013_05
特許番号
US08436009B2

関連ノート

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