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Triethylamine → 4-(3-cyclopropyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide

HRID 1666467
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HRID 1666467 반응식
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:18]=[C:19]([CH:21]=[C:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:20]=2)[O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=2)[CH2:3][CH2:2]1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35](=[O:43])OC2C=CC=CC=2)C=1.C([N:46](CC)CC)C>CS(C)=O.O>[CH:1]1([C:4]2[CH:20]=[C:19]([CH:18]=[C:6]([O:7][C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][N:9]=3)[CH:5]=2)[CH:21]=[C:22]2[CH2:23][CH2:24][N:25]([C:35]([NH:34][C:30]3[N:46]=[N:28][CH:33]=[CH:32][CH:31]=3)=[O:43])[CH2:26][CH2:27]2)[CH2:2][CH2:3]1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 668754182-(3-Cyclopropyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

생성물 1

HCID 249679964-(3-cyclopropyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide수율 66%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 962Water용매

실험 절차

To a solution of 2-(3-cyclopropyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (0.15 g, 0.401 mmol) and phenyl pyridin-3-ylcarbamate (85.8 mg, 0.4 mmol) in DMSO (1.5 mL) was added triethylamine (0.55 mL, 4.0 mmol) and the mixture was stirred overnight. The reaction mixture was diluted with water and extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4, and evaporated to dryness. The residue was purified by silica gel column chromatography (38% acetone in hexane) to give the title compound (0.13 g, 66%). 1H NMR (500 MHz, CDCl3): δ 8.77 (s, 1H), 8.45 (s, 1H), 8.41 (s, 1H), 7.89 (d, J=8.5 Hz, 1H), 7.47 (t, J=4.5 Hz, 1H), 6.99 (d, J=8.5 Hz, 1H), 6.81 (s, 1H), 6.77 (s, 1H), 6.70 (s, 1H), 6.38 (s, 1H), 3.70 (m, 2H), 3.60 (m, 2H), 2.60 (m, 2H), 2.47 (d, 2H), 1.87 (m, 1H), 0.98 (d, J=8 Hz, 2H), 0.70 (d, J=4.5 Hz, 2H). 13C NMR (125 MHz, CDCl3): δ 165.83, 156.60, 153.17, 146.31, 145.54, 138.65, 137.71, 136.70, 128.20, 124.83, 123.63, 118.77, 116.75, 111.30, 45.64, 44.62, 35.73, 29.21, 15.44, 9.51; m/z (496.2, M+ H+); HPLC: 98.6%.

후처리

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel column chromatography (38% acetone in hexane)

출처 및 근거

ORD 기록
ord-e4b0309b35264d6fb87c826d34d5afa4
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044052B2

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