Hydrochloric Acid → HCID 70945249, compound

HRID 518005Notes

Reaction equation

HRID 518005 reaction equation
[NH2:1][C:2]1[C:3]([NH:31][CH3:32])=[CH:4][C:5]([C:10]2[CH:26]=[CH:25][C:13]([O:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:12]([C:27]([F:30])([F:29])[F:28])[CH:11]=2)=[N:6][C:7]=1[C:8]#[N:9].Cl.[N:34]([O-])=O.[Na+]>O1CCOCC1.O>[C:8]([C:7]1[C:2]2[N:1]=[N:34][N:31]([CH3:32])[C:3]=2[CH:4]=[C:5]([C:10]2[CH:26]=[CH:25][C:13]([O:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:12]([C:27]([F:28])([F:29])[F:30])[CH:11]=2)[N:6]=1)#[N:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 67294207HCID 67294207, compound

Product 1

HCID 70945249HCID 70945249, 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-(trifluoromethyl)phenoxy)ethylcarbamate (1.130 mmol, 0.51 g) was dissolved in 1M Hydrochloric Acid (2.259 mmol, 2.259 ml) and dioxane (5 ml). Sodium nitrite (1.582 mmol, 0.109 g) in water (5.00 ml) was added to the reaction mixture and it was stirred at room temperature for 1 hr. 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)ethylcarbamate. (0.61 g)

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid washed with water

Sources & evidence

ORD record
ord-c1b710d6b37943b7ae8c5300693e8b00
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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