Hydrochloric Acid → 6-(4-((2-Methoxyethoxy)methoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

HRID 517945Notes

Reaction equation

HRID 517945 reaction equation
[NH2:1][C:2]1[C:3]([C:27]#[N:28])=[N:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:12]([C:23]([F:26])([F:25])[F:24])[CH:11]=2)=[CH:6][C:7]=1[NH:8][CH3:9].Cl.[N:30]([O-])=O.[Na+]>O1CCOCC1.O>[CH3:22][O:21][CH2:20][CH2:19][O:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:5]2[N:4]=[C:3]([C:27]#[N:28])[C:2]3[N:1]=[N:30][N:8]([CH3:9])[C:7]=3[CH:6]=2)=[CH:11][C:12]=1[C:23]([F:26])([F:24])[F:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 672942413-Amino-6-(4-((2-methoxyethoxy)-methoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)picolinonitrile

Product 1

HCID 533303896-(4-((2-Methoxyethoxy)methoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrileYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

3-amino-6-(4-((2-methoxyethoxy)methoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)picolinonitrile (100 mg) was suspended in dioxane (1500 μl) and water (1500 μl) and cooled to 0° C. Hydrochloric acid (2M, 189 μl) followed by dropwise addition of sodium nitrite (25 mg) in water (500 μl) and the mixture stirred at room temperature for 2 hours. The suspension was filtered and the solid washed with water to afford pale brown solid 6-(4-((2-methoxyethoxy)methoxy)-3-(trifluoromethyl)-phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (92% yield).

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid washed with water

Sources & evidence

ORD record
ord-efdf13160cd34c17a5f84d04eed7952b
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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