Potassium Carbonate → HCID 86625871, compound

HRID 1485579

Reaction equation

HRID 1485579 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.Br[C:16]1[N:17]=[N:18][CH:19]=[CH:20][CH:21]=1.[F-].[Cs+].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl.O>[N:17]1[CH:16]=[CH:21][CH:20]=[C:19]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)[N:18]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 7238334-(N-Boc-amino)piperidineHCID 131266993-Bromopyridazine

Product 1

HCID 86625871HCID 86625871, compoundYield 35.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

The reaction mixture of tert-butyl piperidin-4-ylcarbamate (250 mg, 1.25 mmol), 3-bromopyridazine (258 mg, 1.62 mmol), CsF (37.9 mg, 0.25 mmol), and K2CO3 (518 mg, 3.74 mmol) in DMSO (12.5 mL) was heated at 100° C. for 20 h. Water and DCM were poured into the mixture, and the separated aqueous layer was extracted with DCM, the combined organic layers were dried over Na2SO4, filtered, concentrated in vacuo. The residue was purified by column chromatography (Hexane:EtOAc=1:1) to give tert-butyl 1-(pyridazine-3-yl)piperidin-4-ylcarbamate (123 mg, 35%) as a pale yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 1.45 (9H, s), 1.92-2.12 (2H, m), 3.03-3.17 (2H, m), 3.55-3.80 (2H, m), 4.25-4.38 (2H, m), 4.52 (1H, brs), 6.92 (1H, d, J=9.2 Hz), 7.20 (1H, dd, J=4.4, 9.2 Hz), 8.56 (1H, d, J=4.4 Hz). NH peak was not observed. m/z=279.06 [M+1]+.

Workup

  1. extractionthe separated aqueous layer was extracted with DCM
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (Hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-23525637b4f04fb6a18f2c15dd65498f
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Linked notes

Loading…