Methyl iodide → [3-(4-Methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-[3-(2-methyl-2H-tetrazol-5-yl)-phenyl]-amine

HRID 424404Notes

Reaction equation

HRID 424404 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[N:14]=[C:15]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]5[N:30]=[N:31][NH:32][N:33]=5)[CH:24]=4)[C:16]4[C:21]([C:12]3=[N:11][N:10]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:5][CH:4]=1.CI.[C:36]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:13]3[N:14]=[C:15]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]5[N:30]=[N:31][N:32]([CH3:36])[N:33]=5)[CH:24]=4)[C:16]4[C:21]([C:12]3=[N:11][N:10]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11575700[3-(4-Methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-[3-(2H-tetrazol-5-yl)-phenyl]-amine

Product 1

HCID 11705056[3-(4-Methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-[3-(2-methyl-2H-tetrazol-5-yl)-phenyl]-amineYield 20.5%

Reagents, catalysts & solvents 1

HCID 18184436N,N-dimethylformamide acetoneSolvent

Procedure

To a suspension of [3-(4-methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-[3-(2H-tetrazol-5-yl)-phenyl]-amine (compound T3) (111 mg, 0.25 mmol) in a mixture of DMF/acetone 1:1 (8 mL) are added methyl iodide (79 μg, 1.25 mmol) and K2CO3 (53 mg, 0.37 mmol). The mixture is stirred at room temperature over night. The reaction mixture is concentrated and water is added. The resulting precipitate is filtered and washed with methanol to yield 23 mg of the title compound as white powder.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionwater is added
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with methanol

Sources & evidence

ORD record
ord-fbe4b5baf876440382f949b15e17aa62
Source dataset
uspto-grants-2012_01
Patent number
US08106047B2

Reaction notes

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