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

HRID 2080741노트

반응식

HRID 2080741 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2ab924331b2443efbc096bd2385dff56
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932281B2

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