2-Bromo-1-cyclopropylethan-1-one → HCID 59313175, compound

HRID 2171516Notes

Reaction equation

HRID 2171516 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:7][CH2:6]1)=[O:4].CC1C=C(C)[N:11]([C:15]([NH:17][C:18]([NH:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[S:19])=N)N=1>CS(C)=O>[NH2:11][C:15]1[N:17]=[C:18]([NH:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[S:19][C:2]=1[C:3]([CH:5]1[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 109208412-Bromo-1-cyclopropylethan-1-oneHCID 178426534HCID 178426534, compound

Product 1

HCID 59313175HCID 59313175, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 404 mg (2.48 mmol) of 2-bromo-1-cyclopropylethanone in 15 ml of DMSO is added dropwise to 845 mg (2.48 mmol) of the crude mixture from Example 72A while cooling in ice, and the mixture is then heated at 100° C. for 1 h. The crude mixture is poured into ice-water and extracted three times with ethyl acetate. After the combined organic phases have been dried, the solvent is completely removed and the residue is purified by subsequent purification by preparative HPLC. 428 mg (48% of theory) of the product are obtained as a solid.

Workup

  1. temperaturewhile cooling in ice
  2. extractionextracted three times with ethyl acetate
  3. customAfter the combined organic phases have been dried
  4. customthe solvent is completely removed
  5. customthe residue is purified by subsequent purification by preparative HPLC
  6. custom428 mg (48% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-3b4312b0f37d47d39aa3410cbf77b72b
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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