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Trimethyl orthoformate → N-(4-dipropylaminomethyl-phenyl)-4-{[(1-methylimidazol-2-ylmethyl)-amino]methyl}benzamide

HRID 348744
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인쇄 미리보기

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HRID 348744 반응식
[NH2:1][CH2:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:26][N:27]1[CH:31]=[CH:30][N:29]=[C:28]1[CH:32]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO>[CH2:18]([N:17]([CH2:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([CH2:2][NH:1][CH2:32][C:28]3[N:27]([CH3:26])[CH:31]=[CH:30][N:29]=3)=[CH:25][CH:24]=2)=[CH:11][CH:12]=1)[CH2:21][CH2:22][CH3:23])[CH2:19][CH3:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 9005Trimethyl orthoformateHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 4311764Sodium borohydrideHCID 230791854-aminomethyl-N-(4-dipropylaminomethylphenyl)benzamide

생성물 1

HCID 66941901N-(4-dipropylaminomethyl-phenyl)-4-{[(1-methylimidazol-2-ylmethyl)-amino]methyl}benzamide수율 69.3%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

The compound (290.2 mg) obtained in Example 122-3 was dissolved in methanol (8.71 ml) and added with 1-methyl-2-imidazole carboxaldehyde (141.2 mg) and trimethyl orthoformate (272.2 mg), followed by stirring for 22 hours. The reaction solution was cooled with ice and then added with sodium borohydride (97.0 mg), followed by stirring at room temperature for 0.5 hour. The reaction solution was concentrated under reduced pressure and the residue was then added with water, followed by separation/extraction with chloroform. The organic layer was washed with saturate 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 (256.8 mg) as a yellow oily substance.

후처리

  1. temperatureThe reaction solution was cooled with ice
  2. stirringby stirring at room temperature for 0.5 hour
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionthe residue was then added with water
  5. extractionfollowed by separation/extraction with chloroform
  6. washThe organic layer was washed
  7. concentrationwith saturate saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationfollowed by concentration under reduced pressure
  10. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-fce76dd396064edf99f32554d8a2c03a
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07176227B2

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