Methyl iodide → HCID 69700396, compound

HRID 1061074Notes

Reaction equation

HRID 1061074 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 mg). The resulting mixture was stirred overnight at 80° C. After the reaction mixture was concentrated under reduced pressure, the residue was added with water and the resulting precipitate was collected by filtration. The precipitate was then dissolved in a mixed solvent (1:1) of dichloromethane and methanol, followed by the addition of ethyl acetate. The resulting precipitate was collected by filtration, whereby the title compound (144 mg, 56%) was obtained.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. additionthe residue was added with water
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutionThe precipitate was then dissolved in a mixed solvent (1:1) of dichloromethane and methanol
  5. additionfollowed by the addition of ethyl acetate
  6. filtrationThe resulting precipitate was collected by filtration, whereby the title compound (144 mg, 56%)
  7. customwas obtained

Sources & evidence

ORD record
ord-97a6bcdb51c645dbb160daa80f147b90
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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