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Water → 4-(3-(6-(trifluoromethyl)pyridin-3-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide

HRID 1666435
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HRID 1666435 반응식
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[CH:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[O:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[N:17][CH:18]=2)[CH2:4][CH2:3]1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)[N:27]=1.C(N(CC)CC)C.O>CS(C)=O>[F:21][C:19]([F:22])([F:20])[C:16]1[N:17]=[CH:18][C:13]([O:12][C:11]2[CH:10]=[C:9]([CH:25]=[CH:24][CH:23]=2)[CH:8]=[C:5]2[CH2:6][CH2:7][N:2]([C:33]([NH:32][C:28]3[N:27]=[N:26][CH:31]=[CH:30][CH:29]=3)=[O:34])[CH2:3][CH2:4]2)=[CH:14][CH:15]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 20150036Phenyl pyridazin-3-ylcarbamateHCID 668761645-(3-(Piperidin-4-ylidenemethyl)phenoxy)-2-(trifluoromethyl)pyridine hydrochloride

생성물 1

HCID 249651444-(3-(6-(trifluoromethyl)pyridin-3-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide수율 72.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 5-(3-(piperidin-4-ylidenemethyl)phenoxy)-2-(trifluoromethyl)pyridine hydrochloride (0.100 g), phenyl pyridazin-3-ylcarbamate (0.070 g, 1.2 equiv), and triethylamine (0.083 mL, 2.2 equiv) in dimethyl sulfoxide (2 mL, 0.13 M) was heated to 65° C. for 2 h. The reaction was cooled to room temperature. Water was added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-100% ethyl acetate/dichloromethane) to give the title compound as a white foam (0.089 g, 72% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (2H, t, J=5.5 Hz), 2.56 (2H, t, J=5.6 Hz), 3.60 (2H, t, J=5.8 Hz), 3.69 (2H, t, J=5.8 Hz), 6.37 (1H, s), 6.92 (2H, m), 7.07 (1H, d, J=7.6 Hz), 7.30-7.46 (3H, m), 7.62 (1H, d, J=8.8 Hz), 8.25 (1H, d, J=8.2 Hz), 8.45 (1H, d, J=2.5 Hz), 8.76 (1H, d, J=1.9 Hz).

후처리

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic extracts was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/dichloromethane)

출처 및 근거

ORD 기록
ord-4d2f89c1a6d54372ae7068717e179423
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044052B2

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