1-(3-Hydroxyazetidin-1-yl)ethan-1-one → 1-(3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidin-1-yl)ethan-1-one

HRID 1398663Notes

Reaction equation

HRID 1398663 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8](C(Cl)(Cl)Cl)[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1.[OH:22][CH:23]1[CH2:26][N:25]([C:27](=[O:29])[CH3:28])[CH2:24]1.CC(C)([O-])C.[K+]>CN(C)C=O>[NH2:20][C:16]1[N:15]=[C:14]([N:7]2[C:6]3[CH:21]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[O:22][CH:23]2[CH2:26][N:25]([C:27](=[O:29])[CH3:28])[CH2:24]2)[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 110623451-(3-Hydroxyazetidin-1-yl)ethan-1-oneHCID 23665647Potassium tert-butoxideHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 681817461-(3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidin-1-yl)ethan-1-oneYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (500 mg, 1.23 mmol), 1-(3-hydroxyazetidin-1-yl)ethan-1-one (1 g, 8.69 mmol) and potassium t-butoxide (500 mg, 5.21 mmol) in N,N-dimethylformamide (5 mL) kept under nitrogen in a 30-mL sealed tube was stirred overnight at room temperature. The reaction mixture was filtered through a frit filter and the filtrate was purified on a C18 column (acetonitrile/water, 5:95-80:20) to yield 160 mg (29%) of 1-(3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidin-1-yl)ethan-1-one as a yellow solid. LC-MS: m/z=+403 (M+H)+.

Workup

  1. customsealed tube
  2. filtrationThe reaction mixture was filtered through a frit
  3. filtrationfilter
  4. customthe filtrate was purified on a C18 column (acetonitrile/water, 5:95-80:20)

Sources & evidence

ORD record
ord-7543f9e0fab645c4a26daf3d9ad33797
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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