3-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole → 6-({[5-({[(1,1-Dimethylethyl)(diphenyl)silyl]oxyl}methyl)-1-methyl-1H-[1,2,3]triazol-4-yl]methyl}oxy)-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazine

HRID 2183518Notes

Reaction equation

HRID 2183518 reaction equation
[CH3:1][C:2]([Si:5]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:6][CH2:7][C:8]1[N:12]([CH3:13])[N:11]=[N:10][C:9]=1[CH2:14][OH:15])([CH3:4])[CH3:3].Cl[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]2=[N:39][N:40]=[C:41]([C:42]3[CH:46]=[C:45]([CH3:47])[O:44][N:43]=3)[N:31]2[N:30]=1>>[CH3:4][C:2]([Si:5]([O:6][CH2:7][C:8]1[N:12]([CH3:13])[N:11]=[N:10][C:9]=1[CH2:14][O:15][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]2=[N:39][N:40]=[C:41]([C:42]3[CH:46]=[C:45]([CH3:47])[O:44][N:43]=3)[N:31]2[N:30]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:1])[CH3:3]

Participants

3

Reactant 2

HCID 184275393-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazoleHCID 69793338[5-({[(1,1-Dimethylethyl)(diphenyl)silyl]oxy}methyl)-1-methyl-1h-[1,2,3]triazol-4-yl]methanol

Product 1

HCID 1317249446-({[5-({[(1,1-Dimethylethyl)(diphenyl)silyl]oxyl}methyl)-1-methyl-1H-[1,2,3]triazol-4-yl]methyl}oxy)-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazineYield 96%

Procedure

The reaction was carried out according to Example 1 step 4 using [5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-1-methyl-1H-[1,2,3]triazol-4-yl]methanol (1.20 g, 3.14 mmol) and 6-chloro-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (0.90 mg, 3.14 mmol). The crude residue was purified by column chromatography on silica using 1-2% MeOH/CH2Cl2 containing 1% NH3 to yield the desired phthalazine (1.90 g, 96%). 1H NMR (360 MHz, CDCl3) δ 8.68 (1H, d, J=7.9 Hz), 7.99 (1H, d, J=7.9 Hz), 7.91 (1H, t, J=7.9 Hz), 7.69 (1H, t, J=7.9 Hz), 7.55 (4H, d, J=7.9 Hz), 7.34-7.18 (6H, m), 6.90 (1H, s), 5.43 (2H, s), 4.90 (2H, s), 4.10 (3H, s), 2.58 (3H, s), 0.99 (9H, s). m/z (ES+) 632 (M+2H+).

Workup

  1. customThe crude residue was purified by column chromatography on silica using 1-2% MeOH/CH2Cl2 containing 1% NH3

Sources & evidence

ORD record
ord-b75841cf8a1d4b098f3280085a98bd40
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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