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Ethylene glycol dioxane → 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)isonicotinamide

HRID 2174282
Notes
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Reaction equation

HRID 2174282 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([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:3]=1.[Cu][C:27]#[N:28].C(O)C[OH:31].O1CCOCC1>[Cl-].[Na+].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:4]2[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=2)[C:27]([NH2:28])=[O:31])=[N:9]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 22419261Ethylene glycol dioxaneHCID 690942852-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 690929042-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)isonicotinamideYield 11%

Reagents, catalysts & solvents 1

HCID 57417360
Sodium chloride; water
Solvent

Conditions

Temperature
100 °C

Procedure

To a stirring suspension of 2-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole (I-36, 1 equiv) in ethylene glycol-dioxane (approx. 4:1) in a sealed tube was added copper(I) cyanide (3 equiv). The resultant reaction mixture was heated at 100° C. for 24 hr 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 (ethyl acetate/hexanes) to afford 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)isonicotinamide as a solid in 11% 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-462b5e32433448ea8a0ccb44da82d892
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