Acetic Acid → 3-Amino-6-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indol-2-yl}phthalimide

HRID 21000

反応式

HRID 21000 の反応式
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([CH:22]=O)=[CH:17][CH:16]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[OH:31][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([CH2:22][N:37]2[CH2:38][CH2:39][N:34]([CH2:33][CH2:32][OH:31])[CH2:35][CH2:36]2)=[CH:17][CH:16]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6]

参加物

8

反応物 5

HCID 176Acetic AcidHCID 76771-(2-Hydroxyethyl)piperazineHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866282263-Amino-6-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]phthalimide

生成物 1

HCID 684920373-Amino-6-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indol-2-yl}phthalimide収率 38.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

3-Amino-6-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]phthalimide (45.0 mg, 0.111 mmol) was dissolved in acetonitrile (2 mL), and the solution was added with 1-(2-hydroxyethyl)piperazine (57 mg, 0.440 mmol), acetic acid (0.508 mL, 8.87 mmol) and sodium triacetoxyborohydride (118 mg, 0.557 mmol), followed by stirring at room temperature for 2.5 hours. The reaction mixture was added with water and sodium carbonate, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (hexane/ethyl acetate=4/1, 1/1) to obtain 3-amino-6-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indol-2-yl}phthalimide (22.2 mg, yield 38%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (hexane/ethyl acetate=4/1, 1/1)

出典と根拠

ORDレコード
ord-0a946f786c784e549ef91a1a15cd543b
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

関連ノート

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