Propargyl bromide → HCID 86662771, compound

HRID 2359727Notes

Reaction equation

HRID 2359727 reaction equation
[F:1][CH:2]([F:23])[CH2:3][N:4]1[C:9]2[N:10]=[CH:11][S:12][C:8]=2[C:7]([OH:13])=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[I:20])[S:5]1(=[O:22])=[O:21].C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]#[CH:32]>CN(C=O)C>[F:23][CH:2]([F:1])[CH2:3][N:4]1[C:9]2[N:10]=[CH:11][S:12][C:8]=2[C:7]([O:13][CH2:32][C:31]#[CH:30])=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[I:20])[S:5]1(=[O:21])=[O:22]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 86662768HCID 86662768, compound

Product 1

HCID 86662771HCID 86662771, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg (0.3 mmol) of 1-(2,2-difluoroethyl)-3-(2-iodophenyl)-1H-[1,3]thiazolo[4,5-c][1,2]thiazin-4-ol 2,2-dioxide (compound I-a-14) were dissolved in 3 ml of DMF, and 85 mg of potassium carbonate were added at RT. The reaction mixture was stirred at RT for 5 min, and then 0.035 ml (0.46 mmol) of propargyl bromide was added dropwise. The reaction mixture was stirred at 90° C. for 4 h, then poured onto water and extracted repeatedly with ethyl acetate. The combined organic phases were dried (sodium sulfate) and concentrated to dryness. The residue was purified by means of preparative HPLC(C18—SiO2, gradient acetonitrile/water 20:80 to 100:0). This gave 51 mg of compound I-h-3.

Workup

  1. stirringThe reaction mixture was stirred at 90° C. for 4 h
  2. additionpoured onto water
  3. extractionextracted repeatedly with ethyl acetate
  4. dry with materialThe combined organic phases were dried (sodium sulfate)
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by means of preparative HPLC(C18—SiO2, gradient acetonitrile/water 20:80 to 100:0)

Sources & evidence

ORD record
ord-2664b8ccd5614220927d3f648265c935
Source dataset
uspto-grants-2014_04
Patent number
US08686000B2

Reaction notes

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