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

HRID 348744
ノート
印刷プレビュー

反応式

HRID 348744 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fce76dd396064edf99f32554d8a2c03a
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176227B2

反応ノート

読み込み中…

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