3-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole → 6-[5-(2-(Azetidin-1-yl)ethyl)-1-methyl-1H-[1,2,3]triazol-4-ylmethoxy]-3-(5-methyl-isoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazine

HRID 2183511Notes

Reaction equation

HRID 2183511 reaction equation
[N:1]1([CH2:5][CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[N:9][C:8]=2[CH2:13][OH:14])[CH2:4][CH2:3][CH2:2]1.Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]2=[N:26][N:27]=[C:28]([C:29]3[CH:33]=[C:32]([CH3:34])[O:31][N:30]=3)[N:18]2[N:17]=1>>[N:1]1([CH2:5][CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[N:9][C:8]=2[CH2:13][O:14][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3=[N:26][N:27]=[C:28]([C:29]4[CH:33]=[C:32]([CH3:34])[O:31][N:30]=4)[N:18]3[N:17]=2)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 184275393-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazoleHCID 22473219[5-(2-(Azetidin-1-yl)ethyl)-1-methyl-1h-[1,2,3]triazol-4-yl]methanol

Product 1

HCID 102973226-[5-(2-(Azetidin-1-yl)ethyl)-1-methyl-1H-[1,2,3]triazol-4-ylmethoxy]-3-(5-methyl-isoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazine

Procedure

The reaction was carried out according to Example 1 step 4 using [5-(2-(azetidin-1-yl)ethyl)-1-methyl-1H-[1,2,3]triazol-4-yl]methanol (103 mg, 0.53 mmol) and 6-chloro-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (150 mg, 0.53 mmol). The crude residue was purified by column chromatography on silica using 2% MeOH/CH2Cl2 containing 1% NH3 to yield, after recrystallisation from CH2Cl2/iso-hexanes, the desired phthalazine (104 mg, 44%). 1H NMR (360 MHz, CDCl3) δ 8.68 (1H, d, J=7.9 Hz), 8.19 (1H, d, J=7.9 Hz), 7.95 (1H, t, J=7.9 Hz), 7.78 (1H, t, J=7.9 Hz), 6.95 (1H, s), 5.75 (2H, s), 4.07 (3H, s), 3.11 (4H, t, J=6.9 Hz), 2.84 (2H, t, J=7.1 Hz), 2.65-2.50 (5H, m), 1.99 (2H, quintet, J=6.9 Hz). m/z (ES+) 446 (M+H+).

Workup

  1. customThe crude residue was purified by column chromatography on silica using 2% MeOH/CH2Cl2 containing 1% NH3
  2. customto yield
  3. customafter recrystallisation from CH2Cl2/iso-hexanes

Sources & evidence

ORD record
ord-2d050552c09a4de5bc6099435587c023
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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