4-Pyridinemethanamine → HCID 68430734, compound

HRID 2092115Notes

Reaction equation

HRID 2092115 reaction equation
[Cl:1][C:2]1[C:3](=[O:23])[N:4]([CH2:19][C@@H:20]2[CH2:22][O:21]2)[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18].[N:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][CH:25]=1>C(O)C>[Cl:1][C:2]1[C:3](=[O:23])[N:4]([CH2:19][C@@H:20]([OH:21])[CH2:22][NH:31][CH2:30][C:27]2[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=2)[N:5]=[CH:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][C@@H:13]2[CH2:15][C@@H:11]([C:12]2([CH3:17])[CH3:16])[C@H:10]1[CH3:18]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 86647513HCID 86647513, compound

Product 1

HCID 68430734HCID 68430734, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-2-[(2R)-oxiran-2-ylmethyl]-5-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-3(2H)-one (0.141 mmol) in ethanol (2 mL) was stirred with 1-(pyridin-4-yl)methanamine (17 μL, 0.17 mmol) at 80° C. for 8 hours. After cooling, the reaction solution was concentrated, mixed with water and extracted with ethyl acetate, and the extract was evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography (chloroform/methanol=9/1) to give the desired product (19 mg, 29% yield).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction solution was concentrated
  3. additionmixed with water
  4. extractionextracted with ethyl acetate
  5. customthe extract was evaporated under reduced pressure
  6. customThe residue was purified by preparative thin layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-e80f89698e3d49e78c87bbfcee641800
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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