4-fluoro-5-(tributylstannyl)-1H-pyrazole → N-(4-(Chlorodifluoromethoxy)phenyl)-5-(4-fluoro-1H-pyrazol-5-yl)-6-(3-hydroxyazetidin-1-yl)nicotinamide

HRID 525765노트

반응식

HRID 525765 반응식
[Cl:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:24])[C:12]2[CH:17]=[C:16](I)[C:15]([N:19]3[CH2:22][CH:21]([OH:23])[CH2:20]3)=[N:14][CH:13]=2)=[CH:6][CH:5]=1.[F:27][C:28]1[CH:29]=[N:30][NH:31][C:32]=1[Sn](CCCC)(CCCC)CCCC>>[Cl:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:24])[C:12]2[CH:17]=[C:16]([C:32]3[NH:31][N:30]=[CH:29][C:28]=3[F:27])[C:15]([N:19]3[CH2:22][CH:21]([OH:23])[CH2:20]3)=[N:14][CH:13]=2)=[CH:6][CH:5]=1

참가 물질

3

반응물 2

HCID 111530444-fluoro-5-(tributylstannyl)-1H-pyrazoleHCID 89906873N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxyazetidin-1-yl)-5-iodonicotinamide

생성물 1

HCID 118045004N-(4-(Chlorodifluoromethoxy)phenyl)-5-(4-fluoro-1H-pyrazol-5-yl)-6-(3-hydroxyazetidin-1-yl)nicotinamide

실험 절차

The title compound was prepared in an analogous fashion to that described in Example 92 using N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxyazetidin-1-yl)-5-iodonicotinamide (Stage 88.1) and 4-fluoro-5-(tributylstannyl)-1H-pyrazole. After purification by flash chromatography on silica gel, the residue was dissolved in MeCN (2 mL), sonicated and then stirred at RT for 90 min. The resulting suspension was filtered, washed with MeCN (3 mL) and dried to afford the title product as a white solid. HPLC (Condition 7) tR=5.72 min, UPLC-MS (Condition 8) tR=0.93 min, m/z=454.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 3.53-3.61 (m, 2H) 3.91-4.01 (m, 2H) 4.37-4.47 (m, 1H) 5.57 (br. s, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.83-7.97 (m, 3H) 8.04 (d, J=1.96 Hz, 1H) 8.78 (d, J=1.96 Hz, 1H) 10.23 (br. s, 1H) 13.03 (br. s, 1H).

후처리

  1. customThe title compound was prepared in an analogous fashion to
  2. customAfter purification by flash chromatography on silica gel
  3. dissolutionthe residue was dissolved in MeCN (2 mL)
  4. customsonicated
  5. filtrationThe resulting suspension was filtered
  6. washwashed with MeCN (3 mL)
  7. customdried

출처 및 근거

ORD 기록
ord-ade515e98479442ea4ab44ad0469e124
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340537B2

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