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

HRID 1754275Notes

Reaction equation

HRID 1754275 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][C:12]([N:14]([CH3:16])C)=O.[CH:17]1(N)CC1.CC(O)=O>CN(C=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[N:3]=[C:4]([C:7]2[N:14]([CH:12]3[CH2:11][CH2:17]3)[CH:16]=[N:10][N:9]=2)[S:5][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 31374DimethylacetamideHCID 69828CyclopropylamineHCID 580356604-Bromothiazole-2-carbohydrazide

Product 1

HCID 580356534-bromo-2-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiazole

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

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 4-bromo-2-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiazole (contaminated with DMF.DMA for next step).

Workup

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

Sources & evidence

ORD record
ord-c58007136b15486bbe2fed52c4d9562d
Source dataset
uspto-grants-2015_10
Patent number
US09169243B2

Reaction notes

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