Acetic Acid → 4-bromo-2-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiazole

HRID 2170912Notes

Reaction equation

HRID 2170912 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:7]([NH:9][NH2:10])=O)[S:5][CH:6]=1.[CH3:11][N:12]([CH:14]=O)C.[CH3:16][C:17](N(C)C)=O.C1(N)CC1.CC(O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:3]=[C:4]([C:7]2[N:12]([CH:14]3[CH2:17][CH2:16]3)[CH:11]=[N:10][N:9]=2)[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 22628260N,N-dimethylformamide N,N-dimethylacetamideHCID 580356604-Bromothiazole-2-carbohydrazide

Product 1

HCID 580356534-bromo-2-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiazoleYield 97.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

4-bromothiazole-2-carbohydrazide (620 mg, 2.8 mmol) and toluene (9 mL) were added to a sealable vial, DMF·DMA (920 μL, 6.9 mmol) was added and the reaction was stirred for 5 minutes. Cyclopropyl amine (770 μL, 11 mmol), and AcOH (160 μL, 2.8 mmol) were added and the reaction was heated in a microwave reactor at 150° C. for 30 minutes. The reaction was concentrated and purified by flash chromatography (1→7% MeOH in CH2Cl2) to afford 740 mg of 4-bromo-2-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiazole (contaminated with DMF·DMA, but used directly in next step).

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated
  3. custompurified by flash chromatography (1→7% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b4e7d5dac516430587b4a8cddd3bc1e2
Source dataset
uspto-grants-2015_06
Patent number
US09051313B2

Reaction notes

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