1,2-Dichloroethane → 2-(4-Bromo-3,5-dimethyl-1H-pyrazol-1-yl)-1-(3-hydroxy-1-azetidinyl)ethanone

HRID 58066Notes

Reaction equation

HRID 58066 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[N:4][N:5]([CH2:8][C:9]([OH:11])=O)[C:6]=1[CH3:7].[NH:13]1[CH2:16][CH:15]([OH:17])[CH2:14]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[C:3]([CH3:12])=[N:4][N:5]([CH2:8][C:9]([N:13]2[CH2:16][CH:15]([OH:17])[CH2:14]2)=[O:11])[C:6]=1[CH3:7]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 8196162-(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)acetic acidHCID 15142903-Hydroxyazetidine

Product 1

HCID 897829192-(4-Bromo-3,5-dimethyl-1H-pyrazol-1-yl)-1-(3-hydroxy-1-azetidinyl)ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2-(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)acetic acid (0.4 g, 1.716 mmol) in DMF (6 mL) were added azetidin-3-ol (0.151 g, 2.060 mmol), HOBt (0.301 g, 2.231 mmol), and EDC (0.461 g, 2.403 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (1.495 mL, 8.58 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 to give the title compound, which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-50b2cd0b08494a209af383aea6476a4e
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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