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Triethylamine → (RS)-1-[1-(acenaphthen-1-yl)piperidin-4-yl]-3-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-dihydro-2H-benzoimidazol-2-one Dihydrochloride

HRID 230462
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HRID 230462 반응식
[CH:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH2:28][C:29](O)=[O:30])[C:20]3=[O:32])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.CCN=C=NCCCN(C)C.[ClH:51].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.O>[ClH:51].[ClH:51].[CH:1]1([N:13]2[CH2:14][CH2:15][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH2:28][C:29]([N:37]4[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]4)=[O:30])[C:20]3=[O:32])[CH2:17][CH2:18]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1
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참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23063002(RS)-2-{3-[1-(acenaphthen-1-yl)piperidin-4-yl]-2,3-dihydro-2-oxo-benzoimidazol-1-yl}acetic Acid

생성물 1

HCID 23063003
(RS)-1-[1-(acenaphthen-1-yl)piperidin-4-yl]-3-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-dihydro-2H-benzoimidazol-2-one Dihydrochloride
수율 104.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

(RS)-2-{3-[1-(Acenaphthen-1-yl)piperidin-4-yl]-2,3-dihydro-2-oxo-benzoimidazol-1-yl}acetic acid (0.85 g, 2 mmol) was dissolved in DMF (10 ml). 1-Methylpiperazine (0.2 g, 2 mmol), WSC.HCl (0.46 g, 2.4 mmol), HOBt (0.37 g, 2.4 mmol) and triethylamine (0.53 ml, 3.8 mmol) were added and the mixture was stirred at room temperature for 8 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated aqueous ammonium chloride solution, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) and hydrochloric acid/ethanol was added to give the title compound (0.73 g) as a yellow solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol) and hydrochloric acid/ethanol
  6. additionwas added

출처 및 근거

ORD 기록
ord-09fe8617c24a46098c9166c9dca4dbd4
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07566728B2

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