Methyl iodide → HCID 25206091, compound

HRID 2424407Notes

Reaction equation

HRID 2424407 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:10]1[S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26].[H-].[Na+].CI>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[N:19]2[CH2:20][CH2:21][N:22]([CH3:2])[CH2:23][CH2:24]2)[N:10]1[S:25]([C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25206250HCID 25206250, compound

Product 1

HCID 25206091HCID 25206091, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

0.26 g (0.52 mmol) of 1,2,3,4-tetrahydro-2-methyl-5-(piperazin -1-yl)-1-(4-methylbenzenesulfonyl)quinoline prepared in example 14 and 67 mg (1.56 mmol, 45%) NaH was dissolved in 2 mL DMF at 0° C. After stirring 1 h at 0° C., the mixture was cooled to −78° C. and MeI was added (32 μL, 0.52 mmol). The reaction mixture was stirred over 1 night at room temperature After evaporating the solvent, the residue was dissolved in 15 mL water and extracted with EtOAc. The crude product was purified by column chromatography (eluent: CH2Cl2-MeOH 0.5%). Yield: 82 mg (38%) Rf=0.65 (CH2Cl2-MeOH 9:1).

Workup

  1. temperaturethe mixture was cooled to −78° C.
  2. stirringThe reaction mixture was stirred over 1 night at room temperature
  3. customAfter evaporating the solvent
  4. dissolutionthe residue was dissolved in 15 mL water
  5. extractionextracted with EtOAc
  6. customThe crude product was purified by column chromatography (eluent: CH2Cl2-MeOH 0.5%)

Sources & evidence

ORD record
ord-f07dd324280b48169b5a6dc816330233
Source dataset
uspto-grants-2011_06
Patent number
US07964603B2

Reaction notes

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