Sodium hydride → 6-(1-Methyl-1H-1,2,4-triazol-3-ylmethoxy)-7-phenyl-3-(pyrazin-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 1278565노트

반응식

HRID 1278565 반응식
[CH3:1][N:2]1[CH:6]=[N:5][C:4]([CH2:7][OH:8])=[N:3]1.[H-].[Na+].Cl[C:12]1[C:13]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:14][C:15]2[N:16]([C:18]([C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)=[N:19][N:20]=2)[N:17]=1>CN(C)C=O>[CH3:1][N:2]1[CH:6]=[N:5][C:4]([CH2:7][O:8][C:12]2[C:13]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:14][C:15]3[N:16]([C:18]([C:21]4[CH:26]=[N:25][CH:24]=[CH:23][N:22]=4)=[N:19][N:20]=3)[N:17]=2)=[N:3]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 10351670(1-Methyl-1H-1,2,4-triazol-3-yl)methanolHCID 184306846-Chloro-7-phenyl-3-(pyrazin-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

생성물 1

HCID 98214886-(1-Methyl-1H-1,2,4-triazol-3-ylmethoxy)-7-phenyl-3-(pyrazin-2-yl)-1,2,4-triazolo[4,3-b]pyridazine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (1-methyl-1H-1,2,4-triazol-3-yl)methanol (prepared using the conditions described in EP-A-421210; 0.044 g, 0.39 mmol) in dimethyl formamide (10 ml) was added sodium hydride (0.016 g of a 60% dispersion in oil, 0.390 mmol) and the reaction mixture was stirred at room temperature under nitrogen for 0.5 h. After this time, the product from Example 1 step e) (0.1 g, 0.325 mmol) was added and the reaction mixture stirred for 2.5 h. The solvent was removed under high vacuum. Water (5 ml) was added to the residue and the solid produced was collected by filtration. The solid was recrystallised from ethyl acetate/ethanol to give the required product (0.049 g, m.p. 256.9-257.8° C.). 1H NMR (360 MHz, CDCl3) δ 3.94 (3H, s), 5.62 (2H, s), 7.47 (3H, m), 7.67 (2H, m), 8.04 (1H, s), 8.10 (1H, s), 8.70 (1H, s), 8.84 (1H, s), 9.80 (1H, s) (ES+) m/e 386 [MH+].

후처리

  1. stirringthe reaction mixture stirred for 2.5 h
  2. customThe solvent was removed under high vacuum
  3. additionWater (5 ml) was added to the residue
  4. customthe solid produced
  5. filtrationwas collected by filtration
  6. customThe solid was recrystallised from ethyl acetate/ethanol

출처 및 근거

ORD 기록
ord-8829ac68f9304aa3895ef11dc2ec0790
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06444666B1

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