Hydrochloric Acid → HCID 69932007, compound

HRID 517999Notes

Reaction equation

HRID 517999 reaction equation
[NH2:1][C:2]1[C:3]([NH:32][CH3:33])=[CH:4][C:5]([C:10]2[CH:11]=[N:12][C:13]([O:20][CH2:21][CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=2)=[N:6][C:7]=1[C:8]#[N:9].Cl.[N:35]([O-])=O.[Na+]>O.O1CCOCC1>[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:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[C:13]([O:20][CH2:21][CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[N:12][CH:11]=2)[N:6]=1)#[N:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 70945481HCID 70945481, compound

Product 1

HCID 69932007HCID 69932007, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of tert-butyl 2-(5-amino-6-cyano-4-(methylamino)-5′-(trifluoromethyl)-2,3′-bipyridin-6′-yloxy)ethyl(methyl)carbamate (160 mg) in water (3 ml) and 1,4-dioxane (3 ml), 2N hydrochloric acid (192 mg) was added at 0° C. and sodium nitrite (34.2 mg) in water (1 ml) was added then stirred at 0° C. for 10 min then at 20° C. for 20 h. The reaction mixture was filtered, washed with water, dried in vacuum oven to give 140 mg light yellow solid as tert-butyl 2-(5-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-3-(trifluoromethyl)pyridin-2-yloxy)ethyl(methyl)-carbamate (85%).

Workup

  1. additionwas added at 0° C.
  2. waitat 20° C. for 20 h
  3. filtrationThe reaction mixture was filtered
  4. washwashed with water
  5. customdried in vacuum oven

Sources & evidence

ORD record
ord-bed5aa2551b14779b36a1e5506eba1bf
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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