Hydrochloric Acid → HCID 70945411, compound

HRID 518009Notes

Reaction equation

HRID 518009 reaction equation
[NH2:1][C:2]1[C:3]([NH:32][CH3:33])=[CH:4][C:5]([C:10]2[CH:27]=[CH:26][C:13]([O:14][CH2:15][CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:12]([C:28]([F:31])([F:30])[F:29])[CH:11]=2)=[N:6][C:7]=1[C:8]#[N:9].Cl.[N:35]([O-])=O.[Na+]>O1CCOCC1.O>[C:8]([C:7]1[C:2]2[N:1]=[N:35][N:32]([CH3:33])[C:3]=2[CH:4]=[C:5]([C:10]2[CH:27]=[CH:26][C:13]([O:14][CH2:15][CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[C:12]([C:28]([F:29])([F:30])[F:31])[CH:11]=2)[N:6]=1)#[N:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 67294345HCID 67294345, compound

Product 1

HCID 70945411HCID 70945411, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-(4-(5-amino-6-cyano-4-(methylamino)pyridin-2-yl)-2-(trifluoro-methyl)phenoxy)ethyl(methyl)carbamate (7.43 mmol, 3.46 g) was dissolved in 1M Hydrochloric Acid (14.87 mmol, 14.87 ml) and Dioxane (5 ml). Sodium nitrite (10.41 mmol, 0.718 g) in Water (5.00 ml) was added to the reaction mixture and it was stirred at room temperature for 1 hr. The acetonitrile was removed and the reaction taken up in dioxane/water. The reaction mixture was filtered and the solid washed with water to afford tert-butyl 2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl(methyl)carbamate. (2.82 g)

Workup

  1. customThe acetonitrile was removed
  2. filtrationThe reaction mixture was filtered
  3. washthe solid washed with water

Sources & evidence

ORD record
ord-a9e2f7d6535b4ba3a9b773e9f5ecd711
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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