Acetonitrile → N-[3-[3-(Acetylamino)(imino)methylphenyl]-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamide

HRID 1796194ノート

反応式

HRID 1796194 の反応式
Cl.Cl.C([C:6]1[CH:7]=[C:8](/[CH:12]=[CH:13]/[CH2:14][N:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]3[CH2:32][CH2:31][N:30]([C:33]4[CH2:37][CH2:36][CH2:35][N:34]=4)[CH2:29][CH2:28]3)=[C:22]([C:38](=[O:40])[NH2:39])[CH:21]=2)[S:16]([CH3:19])(=[O:18])=[O:17])[CH:9]=[CH:10][CH:11]=1)(=N)N.C(OC1C=CC([N+]([O-])=O)=CC=1)(=[O:43])C.[CH2:54]([N:56](CC)CC)[CH3:55].[C:61](#[N:63])C>ClCCl.O>[C:54]([NH:56][C:6]1[C:7]([CH:61]=[NH:63])=[C:8](/[CH:12]=[CH:13]/[CH2:14][N:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]3[CH2:32][CH2:31][N:30]([C:33]4[CH2:37][CH2:36][CH2:35][N:34]=4)[CH2:29][CH2:28]3)=[C:22]([C:38](=[O:40])[NH2:39])[CH:21]=2)[S:16]([CH3:19])(=[O:17])=[O:18])[CH:9]=[CH:10][CH:11]=1)(=[O:43])[CH3:55]

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 132434-Nitrophenyl AcetateHCID 22180975N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamide dihydrochloride

生成物 1

HCID 86593749N-[3-[3-(Acetylamino)(imino)methylphenyl]-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamide収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamide dihydrochloride (0.29 g) obtained in example 99(b) in a mixture of dichloromethane (3 ml) and acetonitrile (3 ml) were added successively 4-nitrophenyl acetate (0.09 g) and triethylamine (0.26 ml) with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 4 hours. After stirring, to the reaction mixture was added dichloromethane, and the organic layer was washed successively with a 0.5N aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and methanol (50:0˜47:3). The solid obtained was dissolved in water and then lyophilized to afford the title compound (0.16 g, yield: 58%) as a pale yellow amorphous solid.

後処理

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 4 hours
  3. stirringAfter stirring, to the reaction mixture
  4. washthe organic layer was washed successively with a 0.5N aqueous sodium hydroxide solution
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by chromatography on a silica gel column
  9. customThe solid obtained

出典と根拠

ORDレコード
ord-32b09cbbb31745a0b6f7d73ea045b67e
出典データセット
uspto-grants-2006_04
特許番号
US07030138B2

反応ノート

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