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Oxalyl chloride → 5-Chloro-4,6-dimethyl-2-[4-[(E)-4,4,4-trifluorobut-2-enoyl]piperazin-1-yl]pyridine-3-carbonitrile

HRID 1775358
Notes
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Reaction equation

HRID 1775358 reaction equation
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[Cl:16][C:17]1[C:18]([CH3:32])=[C:19]([C:30]#[N:31])[C:20]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[N:21][C:22]=1[CH3:23].CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C>[Cl:16][C:17]1[C:18]([CH3:32])=[C:19]([C:30]#[N:31])[C:20]([N:24]2[CH2:25][CH2:26][N:27]([C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])[CH2:28][CH2:29]2)=[N:21][C:22]=1[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57096144,4,4-Trifluorocrotonic acidHCID 898255905-Chloro-4,6-dimethyl-2-(piperazin-1-yl)pyridine-3-carbonitrile

Product 1

HCID 717652865-Chloro-4,6-dimethyl-2-[4-[(E)-4,4,4-trifluorobut-2-enoyl]piperazin-1-yl]pyridine-3-carbonitrileYield 5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(E)-4,4,4-Trifluorobut-2-enoic acid (25 mg, 0.18 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (16 μl, 0.18 mol) and one drop of DMF were added and the resulting solution was stirred at room temperature for 10 minutes. This solution was added to a solution of 5-chloro-4,6-dimethyl-2-piperazin-1-yl-pyridine-3-carbonitrile (38 mg, 0.15 mmol) and DIPEA (79 μl, 0.45 mmol) in anhydrous DCM (2 ml) and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 2.7 mg of a solid (0.007 mmol, 5%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record
ord-f428f8eff9414f84a16ccd7023cedb5c
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260441B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes