3-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazole → 1-Methyl-1-{2-[3-(5-methylisoxazol-3-yl)[1,2,4]triazolo[3,4-alpha]phthalazin-6-yloxymethyl]pyridin-5-yl}ethylamine

HRID 2183499Notes

Reaction equation

HRID 2183499 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH2:12])([CH3:11])[CH3:10])=[CH:5][N:4]=1.Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]2=[N:24][N:25]=[C:26]([C:27]3[CH:31]=[C:30]([CH3:32])[O:29][N:28]=3)[N:16]2[N:15]=1>>[CH3:11][C:9]([NH2:12])([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:1][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]3=[N:24][N:25]=[C:26]([C:27]4[CH:31]=[C:30]([CH3:32])[O:29][N:28]=4)[N:16]3[N:15]=2)=[N:4][CH:5]=1)[CH3:10]

Participants

3

Reactant 2

HCID 184275393-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-5-methylisoxazoleHCID 69793455(5-(2-Aminopropan-2-yl)pyridin-2-yl)methanol

Product 1

HCID 698955041-Methyl-1-{2-[3-(5-methylisoxazol-3-yl)[1,2,4]triazolo[3,4-alpha]phthalazin-6-yloxymethyl]pyridin-5-yl}ethylamine

Procedure

The reaction was carried out as described in Example 1, Step 4 using 1-[2-(hydroxymethyl)pyridin-5-yl](1-methyl)ethylamine (330 mg, 1.98 mmol) and 6-chloro-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine to give after column chromatography on silica, eluting with 4% MeOH/CH2Cl2 containing 1% NH3 solution, the title compound (504 mg, 61%) which was recrystallised from CH2Cl2/hexanes.

Workup

  1. customto give after column chromatography on silica
  2. washeluting with 4% MeOH/CH2Cl2 containing 1% NH3 solution
  3. customthe title compound (504 mg, 61%) which was recrystallised from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-d33be2775d984a96b913b2ba1a12a3dc
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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