(Pyridazine-3,6-diyl)dimethanol → HCID 131724949, compound

HRID 2183525Notes

Reaction equation

HRID 2183525 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[N:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.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:1][CH2:2][C:3]4[N:8]=[N:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=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 15275423(Pyridazine-3,6-diyl)dimethanolHCID 184275393-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole

Product 1

HCID 131724949HCID 131724949, compoundYield 12.7%

Procedure

(6-Hydroxymethylpyridazin-3-yl)methanol (J. Het. Chem., 1996, 33 (6), 2059-2061) (0.10 g, 0.71 mmol) and 6-chloro-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (0.22 g, 0.77 mmol) were coupled together and purified as in Example 1, step 4 to give {6-[3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazin-6-yloxymethyl]pyridazin-3-yl}methanol as a white solid (35 mg). 1H NMR (400 MHz, d6-DMSO) δ 2.58 (3H, s), 4.80 (2H, s), 5.65-5.75 (1H, br s), 5.92 (2H, s), 6.99 (1H, s), 7.81 (1H, d, J 8), 7.98 (1H, t, J 8), 8.07-8.15 (2H, m), 8.32 (1H, d, J 8), 8.58 (1H, d, J 8). m/z (ES+) 390 (M+H+).

Workup

  1. custompurified as in Example 1, step 4

Sources & evidence

ORD record
ord-559a327b5b1e41ccba6703041d9aec2f
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

Loading…