3-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole → 6-[5-{1-(Azetidin-1-yl)ethyl}pyridin-2-ylmethyloxyl]-3-(5-methyl isoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazine

HRID 2183491Notes

Reaction equation

HRID 2183491 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2=[N:12][N:13]=[C:14]([C:15]3[CH:19]=[C:18]([CH3:20])[O:17][N:16]=3)[N:4]2[N:3]=1.[N:21]1([CH:25]([C:27]2[CH:28]=[CH:29][C:30]([CH2:33][OH:34])=[N:31][CH:32]=2)[CH3:26])[CH2:24][CH2:23][CH2:22]1>>[N:21]1([CH:25]([C:27]2[CH:28]=[CH:29][C:30]([CH2:33][O:34][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]4=[N:12][N:13]=[C:14]([C:15]5[CH:19]=[C:18]([CH3:20])[O:17][N:16]=5)[N:4]4[N:3]=3)=[N:31][CH:32]=2)[CH3:26])[CH2:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 184275393-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazoleHCID 224732235-[1-(1-Azetidinyl)ethyl]-2-pyridinemethanol

Product 1

HCID 1317249326-[5-{1-(Azetidin-1-yl)ethyl}pyridin-2-ylmethyloxyl]-3-(5-methyl isoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazine

Procedure

The reaction was carried out as described in Example 1, Step 4 using 6-chloro-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (100 mg, 0.35 mmol) and [5-{1-(azetidin-1-yl)ethyl}pyridin-2-yl]methanol (67 mg, 0.35 mmol) to give, after column chromatography on silica, eluting with 2.5% MeOH/CH2Cl2 containing 1% NH3 solution, the amine (121 mg, 79%) which was recrystallised from CH2Cl2/hexane.

Workup

  1. customto give
  2. washafter column chromatography on silica, eluting with 2.5% MeOH/CH2Cl2 containing 1% NH3 solution
  3. customthe amine (121 mg, 79%) which was recrystallised from CH2Cl2/hexane

Sources & evidence

ORD record
ord-f0660e7ebf3248a4a41ee25a7d7ffaab
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

Loading…