Azetidine → HCID 86696137, compound

HRID 1425985Notes

Reaction equation

HRID 1425985 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.[Cl:5][C:6]1[N:7]=[N:8][C:9](Cl)=[CH:10][CH:11]=1.C(N(CC)C(C)C)(C)C>C(O)CC>[N:1]1([C:9]2[N:8]=[N:7][C:6]([Cl:5])=[CH:11][CH:10]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 673313,6-DichloropyridazineHCID 81531Diisopropylethylamine

Product 1

HCID 86696137HCID 86696137, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Azetidine (250 mg) was added to a stirred solution of 3,6-dichloropyridazine (650 mg) and N,N-diisopropyl-ethylamine (0.9 mL) in n-propanol (10 mL). The mixture was stirred at room temperature for 9 days and then concentrated. The solid residue was partitioned between ethyl acetate (100 mL) and water (10 mL). The organic layer was separated and washed with brine (10 mL), dried (Na2SO4), and concentrated to leave a white solid (627 mg). Chromatography on a 12-g silica gel cartridge (eluted with a 0-100% ethyl acetate in hexanes gradient) afforded the title compound as a white solid. Yield: 441 mg (59% of theory); 1H NMR (CDCl3) δ 2.47 (m, 2H), 4.13 (m, 4H), 6.48 (d, 1H), 7.16 (d, 1H).

Workup

  1. concentrationconcentrated
  2. customThe solid residue was partitioned between ethyl acetate (100 mL) and water (10 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd7ddcb144e14e41a9c7e076295cc4a9
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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