Diisopropylethylamine → 1-(3-(fluoro-phenyl)-1H-[1,2,4]-triazol-3-yl]-methanone

HRID 334095Notes

Reaction equation

HRID 334095 reaction equation
FC1C=C([N:8]2[CH:12]=[N:11][C:10]([C:13]([OH:15])=O)=[N:9]2)C=CC=1.CN(C(ON1N=N[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]1=2)=[N+](C)C)C.[B-](F)(F)(F)[F:34].CCN(C(C)C)C(C)C.BrC1C=C(C(N2CCNCC2CC)=O)OC=1Br>CN(C=O)C>[F:34][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:10]1([CH:13]=[O:15])[N:11]=[CH:12][NH:8][NH:9]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866882381-(3-fluorophenyl)-1H-1,2,4-triazole-3-carboxylic acidHCID 86688319(4,5-Dibromo-furan-2-yl)-(2-ethyl-piperazin-1-yl)-methanone

Product 1

HCID 866883181-(3-(fluoro-phenyl)-1H-[1,2,4]-triazol-3-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.24 mmol) 1-(3-fluoro-phenyl)-1H-[1,2,4]-triazole-3-carboxylic acid was stirred with 85 mg (0.27 mmol) TBTU and 0.10 mL (0.57 mmol) DIPEA in 1.5 mL DMF at RT. After 10 min, 89 mg (0.24 mmol) (4,5-dibromo-furan-2-yl)-(2-ethyl-piperazin-1-yl)-methanone was added and the mixture was stirred at RT for 12 h. The reaction mixture was purified by HPLC.

Workup

  1. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-86d122a2b92c412aa3fa4694e3e733e9
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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