3-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole → 6-{1-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1H-[1,2,3]triazol-4-ylmethoxy}-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazine
Reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([CH2:16][OH:17])[N:13]=[N:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2=[N:29][N:30]=[C:31]([C:32]3[CH:36]=[C:35]([CH3:37])[O:34][N:33]=3)[N:21]2[N:20]=1>>[Si:1]([O:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([CH2:16][O:17][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]3=[N:29][N:30]=[C:31]([C:32]4[CH:36]=[C:35]([CH3:37])[O:34][N:33]=4)[N:21]3[N:20]=2)[N:13]=[N:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The reaction was carried out according to Example 1 step 4 using {1-[2-(tert-butyldimethylsilanyloxy)ethyl]-1H-[1,2,3]triazol-4-yl}methanol (1.67 g, 6.49 mmol) and 6-chloro-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (1.85 g, 6.49 mmol). The crude residue was purified by column chromatography on silica using 2-3% MeOH/CH2Cl2 containing 1% NH3 to yield the desired phthalazine (2.82 g, 86%). 1H NMR (400 MHz, CDCl3) δ 8.75-8.70 (2H, m), 8.23 (1H, d, J=8.5 Hz), 7.94 (1H, t, J=8.5 Hz), 7.80 (1H, t, J=8.5 Hz), 6.91 (1H, s), 5.79 (2H, s), 4.46 (2H, t, J=5.7 Hz), 3.99 (2H, t, J=5.2 Hz), 2.60 (3H, s), 0.67 (9H, s), −0.16 (6H, s). m/z (ES+) 507 (M+H+).
Workup
- customThe crude residue was purified by column chromatography on silica using 2-3% MeOH/CH2Cl2 containing 1% NH3
Sources & evidence
- ORD record
- ord-e8cc4ab575ed41cf95273b06452a171c
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900209B2
Reaction notes
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