Carbon Tetrachloride → HCID 90273397, compound

HRID 1053106Notes

Reaction equation

HRID 1053106 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH:17][C:18]([C:20]2[C:21]([NH2:27])=[N:22][CH:23]=[C:24]([Br:26])[CH:25]=2)=O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCN2C(=NCCC2)CC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)(Cl)(Cl)Cl>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[O:15][C:18]([C:20]3[C:21]([NH2:27])=[N:22][CH:23]=[C:24]([Br:26])[CH:25]=3)=[N:17][N:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 90273127HCID 90273127, compound

Product 1

HCID 90273397HCID 90273397, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-[N′-(2-amino-5-bromo-pyridine-3-carbonyl)-hydrazinocarbonyl]-piperidine-1-carboxylic acid tert-butyl ester (1.3 g, 2.939 mmol) in ACN (50 mL) were added DBU (1.68 g, 11.035 mmol), PPh3 (1.95 g, 7.434 mmol) and CCl4 (4 mL, 41.558 mmol) at RT. The reaction mixture was stirred for 18 h at RT. The reaction mixture was poured into ice-water (30 mL), extracted with ethyl acetate (3×50 mL), organic layer was washed with brine dried over anhydrous sodium sulphate concentrated under reduced pressure. Crude compound was purified by column chromatography using 100-200 mesh silica gel. The column was eluted with 40% EtOAc in petroleum ether to afford the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL), organic layer
  2. washwas washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customCrude compound was purified by column chromatography
  6. washThe column was eluted with 40% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-e89a6e263733457bb62922c675857f5e
Source dataset
uspto-grants-2016_07
Patent number
US09393248B1

Reaction notes

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