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Trimethyl orthoformate → [4-(5-{[(Imidazol-2-ylmethyl)-amino]-methyl}-1-methoxyindan-2-yl)-butyl]-dipropylamine

HRID 1174024
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HRID 1174024 반응식
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([O:12][CH3:13])[CH:7]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:6]2.[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO.O>[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH2:30][NH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([O:12][CH3:13])[CH:7]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:6]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 23079237[4-(5-Aminomethyl-1-methoxyindan-2-yl)-butyl]-dipropylamine

생성물 1

HCID 21084440[4-(5-{[(Imidazol-2-ylmethyl)-amino]-methyl}-1-methoxyindan-2-yl)-butyl]-dipropylamine수율 98.1%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

실험 절차

The compound (45.0 mg) obtained in Example 127-13 was dissolved in methanol (2.25 ml) and added with 2-imidazole carboxaldehyde (19.5 mg) and trimethyl orthoformate (43.1 mg), followed by stirring at room temperature for 1 hour. Under ice-cooling, sodium borohydride (15.4 mg) was added to the solution, and the whole was stirred at room temperature for 30 minutes. The reaction solution was added with water and then subjected to separation/extraction with chloroform. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (54.8 mg) as a yellow oily substance.

후처리

  1. temperatureUnder ice-cooling
  2. stirringthe whole was stirred at room temperature for 30 minutes
  3. extractionsubjected to separation/extraction with chloroform
  4. washThe extract was washed with saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-4684c77efa3f43b69396e95fdea47ac6
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07833991B2

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