Sodium hydride → 3-(2-Fluorophenyl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-7-(thien-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 2306587노트

반응식

HRID 2306587 반응식
[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[N:5][CH:4]=[N:3]1.[H-].[Na+].Cl[C:12]1[C:13]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)=[CH:14][C:15]2[N:16]([C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])=[N:19][N:20]=2)[N:17]=1>CN(C=O)C.O>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[N:16]2[N:17]=[C:12]([O:8][CH2:7][C:6]3[N:2]([CH3:1])[N:3]=[CH:4][N:5]=3)[C:13]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)=[CH:14][C:15]2=[N:20][N:19]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 226098966-Chloro-3-(2-fluorophenyl)-7-(thien-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

생성물 1

HCID 226099153-(2-Fluorophenyl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-7-(thien-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (2-methyl-2H-1,2,4-triazol-3-yl)methanol (0.11 g, 1.0 mmol) (prepared using the conditions described in EP-A-421210) in DMF (5 ml) was added sodium hydride (0.04 g of a 60% dispersion in oil, 1 mol eq) and the reaction mixture was stirred at room temperature for 30 min. After this time 6-chloro-3-(2-fluorophenyl)-7-(thien-2-yl)-1,2,4-triazolo[4,3-b]pyridazine (0.19 g, 0.57 mmol) was added and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with water (70 ml) and the precipitate was collected. The solid was purified by boiling in ethyl acetate and collecting the title compound as a yellow solid (0.01 g, 12%). 1H NMR (250 MHz, d6-DMSO) δ 3.83 (3H, s), 5.64 (2H, s), 7.24 (1H, dd, J 4 and 4 Hz), 7.44-7.55 (2H, m), 7.66-7.71 (1H, m), 7.82 (1H, d, J=5 Hz), 7.96-8.01 (3H, m), 8.23 (1H, s). MS (ES+) m/e 408 [MH]+. Anal. Found C, 53.81; H, 3.62; N, 23.42%. C19H14FN7OS.0.9(H2O) requires C, 53.87; H, 3.76; N, 23.14% m.p. 189-190° C.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 18 h
  2. customthe precipitate was collected
  3. customThe solid was purified
  4. customcollecting the title compound as a yellow solid (0.01 g, 12%)

출처 및 근거

ORD 기록
ord-ab9f4f2c95774b7c907423494f2f75f2
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828322B2

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