Acetic Acid → N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-thiazol-2-ylmethylamino]-methyl}-benzamide

HRID 1173854노트

반응식

HRID 1173854 반응식
[C:1]([N:8]([CH2:15][C:16]1[CH:35]=[CH:34][C:19]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:21])=[CH:18][CH:17]=1)[CH2:9][C:10]1[NH:11][CH:12]=[CH:13][N:14]=1)(OC(C)(C)C)=O.C([C:38]1[S:39][CH:40]=[CH:41][N:42]=1)=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:28]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:26][CH2:25][CH2:24][CH2:23][NH:22][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:8]([CH2:9][C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[CH2:1][C:38]2[S:39][CH:40]=[CH:41][N:42]=2)=[CH:35][CH:34]=1)[CH2:29][CH3:30]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 210844754-{[N-Boc-N-(1H-imidazol-2-ylmethyl)amino]methyl}-N-(4-dipropylaminobutyl)benzamide

생성물 1

HCID 10368004N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-thiazol-2-ylmethylamino]-methyl}-benzamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The compound (39.8 mg) obtained in Example 1-3 and 2-formylthiazole (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (16.9 mg) were dissolved in anhydrous methanol (2.0 ml) and then added with sodium cyanoborohydride (18.9 mg). The solution was adjusted to pH 5 with acetic acid and then stirred at room temperature for 39.5 hours. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and then washed with 1 mol/l sodium hydroxide and saturated saline solution, followed by drying with anhydrous magnesium sulfate. The solvent was distilled off and the residue was then treated with hydrochloric acid. The residue was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (9.20 mg) of the subject compound as a white solid.

후처리

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with 1 mol/l sodium hydroxide and saturated saline solution
  5. dry with materialby drying with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. additionthe residue was then treated with hydrochloric acid
  8. customThe residue was purified through silica gel column chromatography (chloroform/methanol/water)

출처 및 근거

ORD 기록
ord-090397ae8f86441d9da7586b0f53db7e
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07833991B2

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