1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 11616280, compound

HRID 552161Notes

Reaction equation

HRID 552161 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=1)=[O:7].C(OC(=O)[NH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(C)(C)C.N12CCCN=C1CCCCC2>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:26]2[CH2:27][CH2:28][CH:23]([NH2:22])[CH2:24][CH2:25]2)=[CH:12][CH:13]=1)=[O:7]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7238334-(N-Boc-amino)piperidineHCID 167337866-chloro-N-(3-methylbutyl)pyridazine-3-carboxamide

Product 1

HCID 11616280HCID 11616280, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 6-chloropyridazine-3-carboxylic acid (3-methylbutyl)amide (0.140 g, 0.610 mmol) in DMF (7 mL) was added piperidin-4-ylcarbamic acid tert-butyl ester (0.146 g, 0.730 mmol), followed by the addition of 1,8-diazabicyclo[5,4,0]undec-7-ene (0.280 mL, 1.84 mmol) and tetra-n-butylammonium iodide (6 mg). The reaction mixture was stirred at 80° C. for 16 hours. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate, then washed with citric acid, sodium bicarbonate and brine solution. The organic layer was separated, and dried over anhydrous Na2SO4, and evaporated. The residue was purified by column chromatography and then treated with trifluoroacetic acid. The title compound was obtained as a white powder in 50% yield (0.090 g). 1H NMR (300 MHz, DMSO-d6) δ 8.75-8.77 (m, 1H), 7.79 (d, J=9.6 Hz, 1H), 7.34 (d, J=9.6 Hz, 1H), 4.29-4.35 (m, 2H), 3.29-3.22 (m, 1H), 3.06-3.12 (m, 1H), 2.85-2.87 (m, 1H), 2.50 (m, 1H), 1.77-1.80 (m, 2H), 1.56-1.64 (m, 4H), 1.40-1.44 (m, 2H), 1.17-1.25 (m, 1H), 0.90 (d, J=6.6 Hz, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with citric acid, sodium bicarbonate and brine solution
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. additiontreated with trifluoroacetic acid

Sources & evidence

ORD record
ord-79b59a3c01974e20ad7f8f7f0f085e49
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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