Pyrazole → HCID 68182683, compound

HRID 524400Notes

Reaction equation

HRID 524400 reaction equation
[NH2:1][C:2]1[S:3][C:4](Br)=[CH:5][N:6]=1.[NH:8]1[CH:12]=[CH:11][CH:10]=[N:9]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:8]1([CH:4]2[S:3][CH:2]([NH2:1])[N:6]=[CH:5]2)[CH:12]=[CH:11][CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 436002-Thiazolamine, 5-bromo-2×

Product 1

HCID 68182683HCID 68182683, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-5-bromothiazole (2.6 g, 14.68 mmol), pyrazole (1 g, 14.68 mmol) and cesium carbonate (11.92 g, 36.7 mmol) in DMF (29 mL) was heated at 55° C. for 1 hr under argon argon atmosphere. After 1 hr, 2-amino-5-bromothiazole (2.6 g, 14.68 mmol) was added and continued for next 1 hr. Reaction mixture was cooled to rt and poured over ice cold water (200 mL), extracted with ethylacetate (4×100 mL), washed with brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Crude compound was purified by silica gel column chromatography using 60% ethyl acetate in hexane as eluent to afford pure 5-pyrazol-1-yl-5H-thiazol-2-amine (0.2 g).

Workup

  1. waitcontinued for next 1 hr
  2. customReaction mixture
  3. extractionextracted with ethylacetate (4×100 mL)
  4. washwashed with brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customCrude compound was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-34d832c7551e4200bdbd33c6e7da285c
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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