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

HRID 1666463노트

반응식

HRID 1666463 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH:19]=[C:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=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>CS(C)=O.O>[Br:1][C:2]1[CH:18]=[C:17]([CH:16]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=2)[CH:3]=1)[CH:19]=[C:20]1[CH2:25][CH2:24][N:23]([C:33]([NH:32][C:28]2[N:27]=[N:26][CH:31]=[CH:30][CH:29]=2)=[O:34])[CH2:22][CH2:21]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 20150036Phenyl pyridazin-3-ylcarbamateHCID 668769892-(3-Bromo-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

생성물 1

HCID 668757084-(3-bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide수율 66%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

2-(3-Bromo-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (0.57 g, 1.379 mmol) and phenyl pyridazin-3-ylcarbamate (0.296 g, 1.38 mmol) were dissolved in DMSO (4 mL). Triethylamine (0.57 mL, 4.13 mmol) was added and the reaction 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 (37% acetone in hexane) to give the title compound (0.486 g, 66%). 1H NMR (500 MHz, DMSO-d6): δ 8.78 (s, 1H), 8.45 (s, 1H), 8.27 (s, 1H), 7.93 (d, J=8.5 Hz, 1H), 7.41 (dd, J=4.75 Hz, 1H), 7.24 (s, 1H), 7.20 (s, 1H), 7.04 (d, J=9 Hz, 1H), 6.94 (s, 1H), 6.35 (s, 1H), 3.69 (m, 2H), 3.60 (m, 2H), 2.58 (m, 2H), 2.17 (m, 2H). 13C NMR (125 MHz, CDCl3): δ 165.16, 156.80, 153.50, 145.43, 140.30, 139.57, 136.97, 128.86, 128.09, 124.66, 123.35, 122.86, 122.49, 122.24, 121.98, 120.73, 111.67, 45.55, 44.52, 35.74, 29.29, 29.18; m/z (534.1, 536.1, M+ H+); HPLC: 99.0%.

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 (37% acetone in hexane)

출처 및 근거

ORD 기록
ord-1f20ca3fed6d47c1b56b174de70afcef
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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