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Acetic Acid → N-(4-dipropylamino-butyl)-4-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzamide

HRID 2080778
ノート
印刷プレビュー

反応式

HRID 2080778 の反応式
[CH2:1]([N:4]([CH2:27][CH2:28][CH3:29])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][CH2:19][C:20]2[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=2)=[CH:13][CH:12]=1)[CH2:2][CH3:3].C([BH3-])#N.[Na+].C(O)(=O)C.[CH3:38][C:39]1[CH:40]=[CH:41][C:42]([CH:45]=O)=[N:43][CH:44]=1>CO.O>[CH2:27]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:19][C:20]2[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=2)[CH2:45][C:42]2[CH:41]=[CH:40][C:39]([CH3:38])=[CH:44][N:43]=2)=[CH:13][CH:12]=1)[CH2:28][CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 104643395-Methylpyridine-2-carbaldehydeHCID 67103805N-(4-dipropylamino-butyl)-4-{[(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzamide

生成物 1

HCID 11627535N-(4-dipropylamino-butyl)-4-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzamide収率 32%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

実験手順

The compound (782 mg) obtained in Example 20-3 was dissolved in anhydrous methanol (12 ml) and then added with sodium cyanoborohydride (380 mg) and acetic acid (1.5 ml). Then, the solution was added with a methanol solution (2.0 ml) containing the compound (289 mg) obtained in Example 20-4 at −10° C. and then stirred at room temperature for 12 hours under a nitrogen atmosphere. After completion of the reaction, water was added thereto to stop the reaction. The solvent was distilled off under reduced pressure and chloroform and a 1 mol/l sodium hydroxide aqueous solution were added to the residue to make the pH of the aqueous layer about 10, followed by extraction of the aqueous layer with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The resultant was then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and then treated with hydrochloric acid, thereby obtaining a hydrochloride (316 mg) of the subject compound as a white solid.

後処理

  1. additionwas added
  2. customthe reaction
  3. distillationThe solvent was distilled off under reduced pressure and chloroform
  4. additiona 1 mol/l sodium hydroxide aqueous solution were added to the residue
  5. extractionfollowed by extraction of the aqueous layer with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationThe resultant was then concentrated under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  10. additiontreated with hydrochloric acid

出典と根拠

ORDレコード
ord-e861a9e05765410ab1998cc8459ea621
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932281B2

反応ノート

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