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Trimethyl orthoformate → 2-{[(1H-imidazol-2-ylmethyl)amino]methyl}-6-(4-dipropylaminobutyl)naphthalene

HRID 1174006
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HRID 1174006 반응식
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:9]=2)[CH:4]=1.C(OC)(OC)OC.[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]=O.[BH4-].[Na+].[Cl-].[NH4+]>CO>[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH2:36][NH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:9]=2)[CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 210843902-Aminomethyl-6-(4-dipropylaminobutyl)naphthalene

생성물 1

HCID 210843702-{[(1H-imidazol-2-ylmethyl)amino]methyl}-6-(4-dipropylaminobutyl)naphthalene
수율 46%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The compound (67.5 mg) obtained in Example 124-4 was dissolved in anhydrous methanol (2.0 ml) and added with trimethyl orthoformate (0.0354 ml) and 2-imidazole carboxaldehyde (20.8 mg), followed by stirring at room temperature for 2 hours under a nitrogen atmosphere. Subsequently, the solution was added with sodium borohydride (12.3 mg) in an ice bath and then stirred at room temperature for 1 hour. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the solution, and the whole was stirred. The solution was subjected to extraction with chloroform and the extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (39.0 mg) as a yellow oily substance.

후처리

  1. stirringstirred at room temperature for 1 hour
  2. customAfter completion of the reaction
  3. stirringthe whole was stirred
  4. extractionThe solution was subjected to extraction with chloroform
  5. washthe extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)

출처 및 근거

ORD 기록
ord-e8fa738f29da466f9b72de1356f4ac18
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07833991B2

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