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Diisopropylethylamine → {4-[1-(3-Chloro-phenyl)-1H-[1,2,4]triazole-3-carbonyl]-2,2-dimethyl-piperazin-1-yl}-(6-methoxy-pyridin-2-yl)-methanone

HRID 334094
Notes
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Reaction equation

HRID 334094 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[N:11][C:10]([C:13]([OH:15])=O)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.[CH3:23][C:24]1([CH3:40])[CH2:29][NH:28][CH2:27][CH2:26][N:25]1[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[N:33]=1)=[O:31].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>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[N:11][C:10]([C:13]([N:28]3[CH2:27][CH2:26][N:25]([C:30]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[N:33]=4)=[O:31])[C:24]([CH3:40])([CH3:23])[CH2:29]3)=[O:15])=[N:9]2)[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 713019271-(3-Chlorophenyl)-1H-1,2,4-triazole-3-carboxylic acidHCID 86688302(2,2-Dimethyl-piperazin-1-yl)-(6-methoxy-pyridin-2-yl)-methanone trifluoroacetate

Product 1

HCID 86688317
{4-[1-(3-Chloro-phenyl)-1H-[1,2,4]triazole-3-carbonyl]-2,2-dimethyl-piperazin-1-yl}-(6-methoxy-pyridin-2-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 50 mg (0.22 mmol) 1-(3-chloro-phenyl)-1H-[1,2,4]-triazole-3-carboxylic acid, 80 mg (0.22 mmol) (2,2-dimethyl-piperazin-1-yl)-(6-methoxy-pyridin-2-yl)-methanone trifluoroacetate, 77 mg (0.24 mmol) TBTU and 0.10 mL (0.58 mmol) DIPEA in 1.5 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-84f2339868ee4ad289f2747736841ba8
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883789B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes