Diisopropylethylamine → 2-(3,5-Bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-(4-(4-methoxy-pyridin-2-yl)-piperazin-1-yl)-ethanone

HRID 336382Notes

Reaction equation

HRID 336382 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:10]([CH2:20][C:21](O)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:55][O:56][C:57]1[CH:62]=[CH:61][N:60]=[C:59]([N:63]2[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]2)[CH:58]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:10]([CH2:20][C:21]([N:66]3[CH2:67][CH2:68][N:63]([C:59]4[CH:58]=[C:57]([O:56][CH3:55])[CH:62]=[CH:61][N:60]=4)[CH2:64][CH2:65]3)=[O:22])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 226481321-(4-Methoxypyridin-2-yl)piperazineHCID 86686517(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid

Product 1

HCID 716681662-(3,5-Bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-(4-(4-methoxy-pyridin-2-yl)-piperazin-1-yl)-ethanoneYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32 mg (3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid was dissolved in 2 mL DMF. 39 mg TBTU and 53 μL DIPEA were added to this solution and the mixture was stirred for a few minutes at RT. Then 24 mg 1-(4-methoxy-pyridin-2-yl)-piperazine was added. The mixture was stirred 1 h at RT. The reaction-solution was evaporated and the residue was purified by HPLC to give 30 mg of the desired compound. Rt: 1.68 (method C), (M+H)+: 491

Workup

  1. stirringThe mixture was stirred 1 h at RT
  2. customThe reaction-solution was evaporated
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-5c3418c407564ac080c60a1abbb0c8f5
Source dataset
uspto-grants-2014_11
Patent number
US08889677B2

Reaction notes

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