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Sodium Hydroxide → 6-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-amine

HRID 2174271
Notes
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Reaction equation

HRID 2174271 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][N: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:5]=[CH:4][CH:3]=1.[OH-].[NH4+:27].[OH-].[Na+]>C(O)CO.O1CCOCC1.[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[S:14][CH:15]=[CH:16][N:17]=2)=[N:12][C:8]([C:6]2[N:7]=[C:2]([NH2:27])[CH:3]=[CH:4][CH:5]=2)=[N:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 867132002-(3-(6-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole

Product 1

HCID 690942396-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compound
Catalyst
HCID 22419261Ethylene glycol dioxaneSolvent

Procedure

To a suspension of 2-(3-(6-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole (I-19) and copper(I) oxide (e.g., about 0.2 eq) in ethylene glycol-dioxane (e.g., about 4:1) in a sealed tube is added ammonium hydroxide solution (e.g., ˜29% in water, ˜30 eq). The resultant mixture is warmed to about 100° C. and stirred at that temperature for about 24 h. The reaction solution is cooled to room temperature, poured into 1N NaOH solution and then extracted with EtOAc. The organic phases are dried, e.g., over Na2SO4 or MgSO4, filtered and concentrated. The crude product is purified using SiO2 chromatography and an appropriate gradient (EtOAc/hexanes) to give 6-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-amine (I-14) as a solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic phases are dried
  3. filtratione.g., over Na2SO4 or MgSO4, filtered
  4. concentrationconcentrated
  5. customThe crude product is purified

Sources & evidence

ORD record
ord-cf582c8eb95c4516b35ee2b1a63d8aff
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09061030B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes