Methyl iodide → HCID 69700396, compound

HRID 352941Notes

Reaction equation

HRID 352941 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]3[S:25][C:26]4[CH2:27][NH:28][CH:29]([CH3:33])[CH2:30][C:31]=4[N:32]=3)=[O:23])[CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.C[I:35].[C:36](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[I-:35].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH2:18][N:19]([C:22]([C:24]3[S:25][C:26]4[CH2:27][NH:28][C:29]([CH3:36])([CH3:33])[CH2:30][C:31]=4[NH+:32]=3)=[O:23])[CH2:20][CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22709656HCID 22709656, compound

Product 1

HCID 69700396HCID 69700396, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In N,N-dimethylformamide (20 ml), 1-[(6-chloronaphthalen-2-yl)sulfonyl]-4-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine hydrochloride (200 mg) was dissolved, followed by the addition of methyl iodide (0.05 ml) and potassium carbonate (79.0 mg). The resulting mixture was stirred overnight at 80° C. The reaction mixture was concentrated under reduced pressure. Water was added to the residue and the precipitate so formed was collected by filtration. The precipitate was dissolved in a 1:1 mixed solution of dichloromethane and methanol. Ethyl acetate was added to the resulting solution and the precipitate thus formed was collected by filtration, whereby the title compound (144 mg, 56%) was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. customthe precipitate so formed
  4. filtrationwas collected by filtration
  5. dissolutionThe precipitate was dissolved in a 1:1 mixed solution of dichloromethane and methanol
  6. additionEthyl acetate was added to the resulting solution
  7. customthe precipitate thus formed
  8. filtrationwas collected by filtration, whereby the title compound (144 mg, 56%)
  9. customwas obtained

Sources & evidence

ORD record
ord-694ba635c88c46d38647015073759df9
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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