Acetic Acid → 4-Chloro-7-[1-(tert-butoxycarbonyl)-5-(piperidin-4-ylaminomethyl)indol-2-yl]isoindolinone

HRID 21069

反応式

HRID 21069 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].[NH2:30][CH:31]1[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]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>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

参加物

8

反応物 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

生成物 1

HCID 684890754-Chloro-7-[1-(tert-butoxycarbonyl)-5-(piperidin-4-ylaminomethyl)indol-2-yl]isoindolinone収率 194.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (34.5 mg, 0.0840 mmol) was dissolved in acetonitrile (1 mL), and the solution was treated with 4-amino-1-(tert-butoxycarbonyl)piperidine (70.1 mg, 0.350 mmol), acetic acid (0.100 mL, 1.74 mmol) and sodium triacetoxyborohydride (44.0 mg, 0.208 mmol). The reaction mixture was added with water and sodium carbonate to adjust the pH to 9. The mixture was 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 to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-5-(piperidin-4-ylaminomethyl)indol-2-yl]isoindolinone (80.8 mg).

後処理

  1. extractionThe mixture was extracted 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

出典と根拠

ORDレコード
ord-cd8b6e1e99af4e1ea32745caf4838f35
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

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