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

HRID 517993Notes

Reaction equation

HRID 517993 reaction equation
[NH2:1][C:2]1[C:3]([C:24]#[N:25])=[N:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[CH:6][C:7]=1[NH:8][CH3:9].Cl.[N:27]([O-])=O.[Na+]>O1CCOCC1.O>[OH:19][CH2:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:5]2[N:4]=[C:3]([C:24]#[N:25])[C:2]3[N:1]=[N:27][N:8]([CH3:9])[C:7]=3[CH:6]=2)=[CH:11][C:12]=1[C:20]([F:23])([F:21])[F:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 709451293-Amino-6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)-picolinonitrile

Product 1

HCID 672942706-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrileYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

3-Amino-6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)-picolinonitrile (11 g) was dissolved in dioxane (20 ml), and water (20 ml). 1M HCl (16.39 ml) was added. Sodium nitrite (2.111 g) in water (2 mL) was added and reaction mixture was stirred at room temperature for 2 hrs. Product crashed out and was filtered, washed with water, ether and dried in oven to give 6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (5.7 g) as a pale brown solid. 1H NMR (MeOH) δ: 8.55 (s, 1H), 8.43 (m, 2H), 7.36 (d, 1H), 4.45 (s, 3H), 4.25 (t, 2H), 3.95 (t, 2H). MS m/z 364 (M+H).

Workup

  1. customreaction mixture
  2. filtrationwas filtered
  3. washwashed with water, ether
  4. customdried in oven

Sources & evidence

ORD record
ord-801eaf97cadf4df1bc8a397fd519862b
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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