Ammonium Hydroxide → HCID 69093139, compound

HRID 2174286Notes

Reaction equation

HRID 2174286 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:12]=[C:11]([C:13]3[N:14]=[CH:15][S:16][CH:17]=3)[N:10]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[N:9]=2)[CH:3]=1.[OH-].[NH4+:27]>C(O)CO.O1CCOCC1.[Cl-].[Na+].O.[Cu-]=O>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:10]1[C:11]([C:13]2[N:14]=[CH:15][S:16][CH:17]=2)=[N:12][C:8]([C:4]2[CH:3]=[C:2]([NH2:27])[CH:7]=[CH:6][N:5]=2)=[N:9]1

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 69093586HCID 69093586, compound

Product 1

HCID 69093139HCID 69093139, compoundYield 59.6%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 22419261Ethylene glycol dioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring suspension of 4-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole (I-51, 1 eq) and copper(I) oxide (1 eq) in ethylene glycol-dioxane (approx. 4:1) in a sealed tube was added ammonium hydroxide. The resultant reaction mixture was heated at 100° C. for 12 h and then cooled to room temperature, treated with brine and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified using SiO2 chromatography (methylene chloride/acetonitrile/methanol) to afford 2-(1-(2-fluorobenzyl)-5-(thiazol-4-yl)-1H-1,2,4-triazol-3-yl)pyridin-4-amine as a solid in 59.6% yield.

Workup

  1. customThe resultant reaction mixture
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-c13fa0fed2db4d09ab4b136ac390eb16
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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