Sodium Hydroxide → N-(4-dipropylaminomethylphenyl)-4-{[(1H-imidazol-2-ylmethyl)-(6-methylpyridin-2-ylmethyl)-amino]-methyl}-benzamide

HRID 1173900ノート

反応式

HRID 1173900 の反応式
C(N(CCC)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][CH2:21][C:22]3[NH:23][CH:24]=[CH:25][N:26]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)CC.[CH3:31][C:32]1[N:37]=[C:36]([CH:38]=O)[CH:35]=[CH:34][CH:33]=1.[C:40]([BH3-])#[N:41].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH2:6]([N:41]([CH2:40][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][N:20]([CH2:21][C:22]3[NH:26][CH:25]=[CH:24][N:23]=3)[CH2:38][C:36]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:31])[N:37]=3)=[CH:17][CH:18]=2)=[CH:9][CH:10]=1)[CH2:7][CH2:8][CH3:9])[CH2:5][CH3:10]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084514N-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamide

生成物 1

HCID 9984316N-(4-dipropylaminomethylphenyl)-4-{[(1H-imidazol-2-ylmethyl)-(6-methylpyridin-2-ylmethyl)-amino]-methyl}-benzamide

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

The compound (104.9 mg) obtained in Example 47-3 was dissolved in methanol (3.2 ml) and then added with 6-methylpyridine-2-carboxaldehyde (36.3 mg) and sodium cyanoborohydride (31.4 mg). Then, the solution was adjusted to pH 5 with acetic acid and then stirred at room temperature for 14 hours. After completion of the reaction, a 1 mol/l sodium hydroxide aqueous solution was added to the reaction solution, followed by separation/extraction with chloroform. The organic layer was dried with anhydrous sodium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and then treated with hydrochloric acid, thereby obtaining hydrochloride (75.9 mg) of the subject compound as a white solid.

後処理

  1. customAfter completion of the reaction
  2. extractionfollowed by separation/extraction with chloroform
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationthe solvent was then distilled off
  5. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  6. additiontreated with hydrochloric acid

出典と根拠

ORDレコード
ord-eda859ec231a47bb8f8e96b592163e8b
出典データセット
uspto-grants-2010_11
特許番号
US07833991B2

反応ノート

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