Trimethyl orthoformate → [4-(6-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-inden-2-yl)-butyl]-dipropyl-amine

HRID 2080741ノート

反応式

HRID 2080741 の反応式
[NH2:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:9]2)=[CH:5][CH:4]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[C:24]1[CH:28]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO>[NH:23]1[CH:27]=[CH:26][N:25]=[C:24]1[CH2:28][NH:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:9]2)=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 23155401[4-(6-aminomethyl-1H-inden-2-yl)-butyl]-dipropyl-amine

生成物 1

HCID 23155525[4-(6-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-inden-2-yl)-butyl]-dipropyl-amine収率 53.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The compound (40.1 mg) obtained in Example 11-13 was dissolved in methanol (2.0 ml) and added with 2-imidazole carboxaldehyde (19.2 mg) and trimethyl orthoformate (42.5 mg) and the whole was stirred at room temperature for 30 minutes. Subsequently, the solution was added with sodium borohydride (15.1 mg) under ice-cooling, followed by stirring at room temperature for additional 30 minutes. The reaction solution was concentrated under reduced pressure. The residue was added with water, and extracted with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (27.3 mg) as a yellow oily substance.

後処理

  1. temperaturecooling
  2. stirringby stirring at room temperature for additional 30 minutes
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionThe residue was added with water
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationfollowed by concentration under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

出典と根拠

ORDレコード
ord-2ab924331b2443efbc096bd2385dff56
出典データセット
uspto-grants-2011_04
特許番号
US07932281B2

反応ノート

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