Diisopropylethylamine → (S)-[4-(4,5-Dibromo-furan-2-carbonyl)-3-methyl-piperazin-1-yl]-[1-(3-fluoro-phenyl)-1H-[1,2,4]triazol-3-yl]-methanone

HRID 334093Notes

Reaction equation

HRID 334093 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[N:11][C:10]([C:13]([N:15]3[CH2:20][CH2:19][NH:18][C@@H:17]([CH3:21])[CH2:16]3)=[O:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Br:22][C:23]1[CH:24]=[C:25]([C:29](O)=[O:30])[O:26][C:27]=1[Br:28].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:22][C:23]1[CH:24]=[C:25]([C:29]([N:18]2[CH2:19][CH2:20][N:15]([C:13]([C:10]3[N:11]=[CH:12][N:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)[N:9]=3)=[O:14])[CH2:16][C@@H:17]2[CH3:21])=[O:30])[O:26][C:27]=1[Br:28]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 41948324,5-Dibromofuran-2-carboxylic acidHCID 86688316[1-(3-fluoro-phenyl)-1H-[1,2,4]triazol-3-yl]-((S)-3-methyl-piperazin-1-yl)-methanone

Product 1

HCID 86688315(S)-[4-(4,5-Dibromo-furan-2-carbonyl)-3-methyl-piperazin-1-yl]-[1-(3-fluoro-phenyl)-1H-[1,2,4]triazol-3-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 87 mg (0.30 mmol) [1-(3-fluoro-phenyl)-1H-[1,2,4]triazol-3-yl]-((S)-3-methyl-piperazin-1-yl)-methanone, 84 mg (0.30 mmol) 4,5-dibromo-2-furoic acid, 0.11 g (0.33 mmol) TBTU and 80 μL (0.45 mmol) DIPEA in 5.0 mL DMF 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-bfd68f38074845479012c62b86bf3ca0
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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