1,2-Dichloroethane → (5-Bromo-6-methyl-2-(methylamino)pyridin-3-yl)(3-hydroxyazetidin-1-yl)methanone

HRID 58067Notes

Reaction equation

HRID 58067 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[N:4][C:5]([NH:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(C(C)C)C(C)C)C>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[C:6]([C:7]([N:14]2[CH2:17][CH:16]([OH:18])[CH2:15]2)=[O:9])[C:5]([NH:11][CH3:12])=[N:4][C:3]=1[CH3:13]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 15142903-HydroxyazetidineHCID 897817895-Bromo-6-methyl-2-(methylamino)nicotinic acid

Product 1

HCID 89781760(5-Bromo-6-methyl-2-(methylamino)pyridin-3-yl)(3-hydroxyazetidin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-bromo-6-methyl-2-(methylamino)nicotinic acid (0.2 g, 0.816 mmol) in DMF (3 mL) were added azetidin-3-ol (0.119 g, 1.632 mmol), HOBt (0.154 g, 1.143 mmol), and EDC (0.235 g, 1.224 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (0.426 mL, 2.448 mmol). The reaction mixture was stirred for 18 hours at room temperature. The crude reaction mixture was subsequently diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated by rotary evaporation to give the title compound, which was used without further purification (0.15 g).

Workup

  1. customThe crude reaction mixture
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-e838596aa06443cf9285349e5594f4ae
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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