Pyridine → HCID 67341642, compound

HRID 1846652Notes

Reaction equation

HRID 1846652 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.N1C=CC=CC=1.[CH3:49][N:50]1[CH2:56][CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][C:15]([N:53]3[CH2:54][CH2:55][CH2:56][N:50]([CH3:49])[CH2:51][CH2:52]3)=[O:17])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 2283491-MethylhomopiperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 71238374HCID 71238374, compound

Product 1

HCID 67341642HCID 67341642, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.350 g (1.02 mmol) of (5′-bromo-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid in dimethylformamide (5 mL) is added 0.450 g (1.19 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate followed by 0.380 mL (2.13 mmol) of pyridine. The mixture is stirred at room temperature for 1 hour then 0.225 mg (1.97 mmol) of N-methylhomopiperizine is added and the mixture is stirred at room temperature for 1 h. The mixture is diluted with water and extracted with ethyl acetate. The combined organic phase is washed with water followed by brine then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 0.310 g (69.2%) of 2-(5′-bromo-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-1-(4-methyl-[1,4]diazepan-1-yl)-ethanone as an orange oil.

Workup

  1. stirringthe mixture is stirred at room temperature for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase is washed with water
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-ad03fd88daf54ebba6e26ab70bc6767a
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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