Phenyl 6-methoxypyridin-3-ylcarbamate → 4-(fluoro(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)-N-(6-methoxypyridin-3-yl)piperidine-1-carboxamide

HRID 1666492

반응식

HRID 1666492 반응식
[F:1][C:2](=[C:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=1.[CH3:26][O:27][C:28]1[N:33]=[CH:32][C:31]([NH:34][C:35](=O)[O:36]C2C=CC=CC=2)=[CH:30][CH:29]=1>CS(C)=O.C(N(CC)CC)C.O>[F:1][C:2]([C:3]1[CH:19]=[CH:18][CH:17]=[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:15])([F:16])[F:14])=[CH:9][N:8]=2)[CH:4]=1)=[C:20]1[CH2:25][CH2:24][N:23]([C:35]([NH:34][C:31]2[CH:32]=[N:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)=[O:36])[CH2:22][CH2:21]1

참가 물질

6

반응물 2

HCID 20185962Phenyl 6-methoxypyridin-3-ylcarbamateHCID 668762662-(3-(Fluoro(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine

생성물 1

HCID 249676364-(fluoro(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)-N-(6-methoxypyridin-3-yl)piperidine-1-carboxamide수율 44.7%

시약·촉매·용매 3

HCID 8471Triethylamine촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

To a solution of 2-(3-(fluoro(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine (110 mg, 0.312 mmol) and phenyl 6-methoxypyridin-3-ylcarbamate (76.2 mg, 0.312 mmol) in DMSO (5 mL) under a N2 atmosphere was added 5 drops of triethyl amine and the reaction mixture was stirred for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water several times to remove the excess DMSO. The title compound was crystallized from hexane and diethyl ether to give the pure title compound (70 mg). 1H NMR (500 MHz, CDCl3): δ 2.5 (brs, 2H), 2.6 (brs, 2H), 3.5 (brs, 2H), 3.6 (brs, 2H), 4.0 (s, 3H), 6.7 (d, 1H, J=9 Hz), 7.0 (d, 1H, J=8.5 Hz), 7.1-7.3 (m, 3H), 7.4 (t, 1H, J=8.5 Hz), 7.9 (m, 1H), 8.1 (s, 1H), 8.4 (s, 1H); 13CNMR (125 MHz, CDCl3): 25.5, 27.7, 29.7, 44.0, 44.3, 53.8, 60.4, 110.3, 111.6, 114.2, 114.3, 121.3, 121.4, 121.7, 122.0, 122.5, 124.7, 125.3, 129.6, 129.9, 133.6, 133.8, 134.1, 136.8, 138.5, 145.3, 145.4, 149.9, 151.8, 153.0, 155.2, 160.3, 165.4; m/z (503.3 M+ H+); HPLC: 97.6%.

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water several times
  3. customto remove the excess DMSO
  4. customThe title compound was crystallized from hexane and diethyl ether

출처 및 근거

ORD 기록
ord-8919ee98671b4b708b8c8a5373c90fa1
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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