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Acetic Acid → 4-bromo-N-(5-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamide

HRID 2091612
Notes
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Reaction equation

HRID 2091612 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:15]=[C:14]([C:16]([NH:18][NH2:19])=O)[S:13][CH:12]=2)=[O:9])[CH:3]=1.C[N:21]([CH3:25])[C:22](=O)[CH3:23].[CH3:26]N(C)C=O.C1(N)CC1.C(O)(=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:15]=[C:14]([C:16]3[N:21]([CH:22]4[CH2:26][CH2:23]4)[CH:25]=[N:19][N:18]=3)[S:13][CH:12]=2)=[O:9])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 22628260N,N-dimethylformamide N,N-dimethylacetamideHCID 666284524-bromo-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamide

Product 1

HCID 580356474-bromo-N-(5-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamideYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
145 °C

Procedure

The 4-bromo-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamide (600 mg, 1.8 mmol) and toluene (9 mL) were added to a sealable vial, N,N-dimethylformamide N,N-dimethylacetamide (600 μL, 4.5 mmol) was added and the reaction was stirred for 5 minutes. Cyclopropyl amine (490 μL, 7.2 mmol), and acetic acid (100 μL, 1.8 mmol) were added and the reaction was heated in a microwave reactor at 145° C. for 30 minutes. The solvent was removed under reduced pressure, and the product, 4-bromo-N-(5-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamide 350 mg (50%), was isolated by precipitation from acetonitrile/methanol. Alternatively, the reaction mixture may be purified by flash chromatography. M+1=390.1

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-347458d4a5af43aa8eda8d12ceacf3e9
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440665B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes