3-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole → HCID 131724946, compound

HRID 2183522Notes

Reaction equation

HRID 2183522 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1)=[CH2:2].Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]2=[N:22][N:23]=[C:24]([C:25]3[CH:29]=[C:28]([CH3:30])[O:27][N:26]=3)[N:14]2[N:13]=1>>[CH3:30][C:28]1[O:27][N:26]=[C:25]([C:24]2[N:14]3[N:13]=[C:12]([O:10][CH2:9][C:6]4[CH:7]=[N:8][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=4)[C:21]4[C:16]([C:15]3=[N:22][N:23]=2)=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:29]=1

Participants

3

Reactant 2

HCID 184275393-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazoleHCID 22473202(6-Ethenylpyridin-3-yl)methanol

Product 1

HCID 131724946HCID 131724946, compoundYield 92.1%

Procedure

The reaction was carried out according to Example 1 step 4 using (6-vinylpyridin-3-yl)methanol (500 mg, 3.7 mmol) and 6-chloro-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (1.05 g, 3.7 mmol). The crude residue was purified by column chromatography on silica using 2-4% MeOH/CH2Cl2 to yield the desired phthalazine (1.31 g, 92%). 1H NMR (360 MHz, CDCl3) δ 8.86 (1H, s), 8.68 (1H, d, J=8.0 Hz), 8.21 (1H, d, J=8.0 Hz), 8.03 (1H, dd, J=8.0, 2.2 Hz), 7.95 (1H, t, J=8.0 Hz), 7.80 (1H, t, J=8.0 Hz), 7.40 (1H, d, J=8.0 Hz), 6.88-6.78 (2H, m), 6.23 (1H, dd, J=17.5, 1.1 Hz), 5.68 (2H, s), 5.51 (1H, dd, J=10.8, 1.1 Hz), 2.59 (3H, s). m/z (ES+) 385 (M+2H+).

Workup

  1. customThe crude residue was purified by column chromatography on silica using 2-4% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-9e740ba3705c401eb24c6fac4b4cfbd6
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

Loading…