Piperidine → N-(1-(4-((4-(piperidine-1-carbonyl)phenyl)ethynyl)phenyl)propan-2-yl)acetamide

HRID 76187Notes

Reaction equation

HRID 76187 reaction equation
[C:1]([NH:4][CH:5]([CH3:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].CN(C(ON1N=[N:40][C:35]2C=[CH:37][CH:38]=[CH:39][C:34]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1CCCCC1>CN(C=O)C>[N:40]1([C:19]([C:18]2[CH:17]=[CH:16][C:15]([C:14]#[C:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH3:24])=[CH:12][CH:11]=3)=[CH:23][CH:22]=2)=[O:21])[CH2:37][CH2:38][CH2:39][CH2:34][CH2:35]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666105904-((4-(2-Acetamidopropyl)phenyl)ethynyl)benzoic acid

Product 1

HCID 66611192N-(1-(4-((4-(piperidine-1-carbonyl)phenyl)ethynyl)phenyl)propan-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 30 mg (0.10 mmol) 4-((4-(2-acetamidopropyl)phenyl)ethynyl)benzoic acid (I72.2) in 1 mL DMF are added 20.0 μl (0.10 mmol) TEA and 50 mg (0.15 mmol) TBTU. The mixture is stirred at r.t. for 5 min before it is added to 10 mg (0.12 mmol) piperidine in 500 μl DMF. After stirring at r.t. for 72 h the mixture is purified by HPLC (MeOH/H2O/NH3).

Workup

  1. stirringAfter stirring at r.t. for 72 h the mixture
  2. customis purified by HPLC (MeOH/H2O/NH3)

Sources & evidence

ORD record
ord-15e7a52d0df64fe2b41a392976651de6
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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