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Trifluoromethanesulfonic acid → 1-{5-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-5-methylimidazolidin-2-one

HRID 2411783
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HRID 2411783 반응식
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH:27]([CH3:28])[CH2:26][N:25](CC5C=CC(OC)=CC=5)[C:24]4=[O:38])=[N:21][CH:22]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[CH3:1][C:2]1[C:3]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH:27]([CH3:28])[CH2:26][NH:25][C:24]4=[O:38])=[N:21][CH:22]=3)=[O:16])[CH2:13][CH2:14]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1
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참가 물질

5

반응물 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 712521883-{5-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-1-(4-methoxybenzyl)-4-methylimidazolidin-2-one

생성물 1

HCID 712520091-{5-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-5-methylimidazolidin-2-one수율 82%

시약·촉매·용매 1

HCID 6422
Trifluoroacetic acid
용매

실험 절차

Using (6-bromopyridin-3-yl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (150 mg) described in Preparation Example 127 and 1-(4-methoxybenzyl)-4-methylimidazolidin-2-one (106 mg) described in Preparation Example 52 and by the reaction and treatment in the same manner as in Example 1, 3-{5-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-1-(4-methoxybenzyl)-4-methylimidazolidin-2-one (132 mg) was obtained. The obtained 3-{5-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}-1-(4-methoxybenzyl)-4-methylimidazolidin-2-one (132 mg) was dissolved in trifluoroacetic acid (2 mL), trifluoromethanesulfonic acid (0.11 mL) was added, and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added 5% aqueous sodium hydrogen carbonate solution, and the solvent was evaporated, and the mixture was extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium hydrogen carbonate solution and saturated brine, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol) to give the title compound (83 mg).

후처리

  1. customthe solvent was evaporated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 5% aqueous sodium hydrogen carbonate solution and saturated brine
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol)

출처 및 근거

ORD 기록
ord-69983ab8bb744d2ca1228250188c32e8
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08816079B2

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