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Ammonium Hydroxide → 2-(1-(2-fluorobenzyl)-5-(oxazol-4-yl)-1H-1,2,4-triazol-3-yl)pyridin-4-amine

HRID 2174284
Notes
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Reaction equation

HRID 2174284 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][O: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][O: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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 690943024-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)oxazole

Product 1

HCID 690937872-(1-(2-fluorobenzyl)-5-(oxazol-4-yl)-1H-1,2,4-triazol-3-yl)pyridin-4-amineYield 41.2%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalyst
HCID 22419261
Ethylene glycol dioxane
Solvent
HCID 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)oxazole (I-54, 1 eq) and copper(I) oxide (0.2 eq) in ethylene glycol-dioxane (approx. 4:1) in a sealed tube was added ammonium hydroxide (30 eq). The resultant reaction mixture was heated at 100° C. for 12 hr. The reaction was cooled to room temperature and treated with brine and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified using SiO2 chromatography (DCM/CAN/MeOH) to afford 2-(1-(2-fluorobenzyl)-5-(oxazol-4-yl)-1H-1,2,4-triazol-3-yl)pyridin-4-amine in 41.2% yield.

Workup

  1. customThe resultant reaction mixture
  2. temperatureThe reaction was cooled 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-df5893ef685d445eb27c6fbe07cf12d7
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09061030B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes