Sodium Nitrite → HCID 70945099, compound

HRID 517974Notes

Reaction equation

HRID 517974 reaction equation
[NH2:1][C:2]1[C:3]([NH:36][CH3:37])=[CH:4][C:5]([C:10]2[CH:11]=[N:12][C:13]([O:20][CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=2)=[N:6][C:7]=1[C:8]#[N:9].[N:38]([O-])=O.[Na+]>O.O1CCOCC1>[C:8]([C:7]1[C:2]2[N:1]=[N:38][N:36]([CH3:37])[C:3]=2[CH:4]=[C:5]([C:10]2[CH:15]=[C:14]([C:16]([F:17])([F:19])[F:18])[C:13]([O:20][CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:25][CH2:24]3)=[N:12][CH:11]=2)[N:6]=1)#[N:9]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 70945532HCID 70945532, compound

Product 1

HCID 70945099HCID 70945099, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of tert-butyl 4-(2-(5-amino-6-cyano-4-(methylamino)-5′-(trifluoromethyl)-2,3′-bipyridin-6′-yloxy)ethyl)piperidine-1-carboxylate (5.20 g) in water (40 ml) and 1,4-dioxane (40 ml) was added 2N hydrichloric acid (6.89 ml) at 0° C. To above suspension was then added dropwise sodium nitrite (0.92 g) in water (10 ml). The mixture was then stirred at 0° C. for 10 min and at 20° C. for 16 h. The solid product was collected by filtration and washed with water, dried in vacuum oven to give 4.61 g tert-butyl 4-(2-(5-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-3-(trifluoro-methyl)pyridin-2-yloxy)ethyl)piperidine-1-carboxylate (94%).

Workup

  1. filtrationThe solid product was collected by filtration
  2. washwashed with water
  3. customdried in vacuum oven

Sources & evidence

ORD record
ord-6851d3ec4e2e4620887f56fa6bc0fe40
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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