Water → HCID 68494659, compound

HRID 1038773Notes

Reaction equation

HRID 1038773 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([NH:13][C:14]1[CH:15]=[N:16][C:17]([O:20][C:21]2[CH:29]=[C:28]3[C:24]([CH:25]=[C:26]([C:31]([N:33]4[CH2:38][CH2:37][N:36]([CH2:39][C:40]5[CH:45]=[CH:44][C:43]([O:46][CH2:47][C:48]([F:51])([F:50])[F:49])=[CH:42][CH:41]=5)[CH2:35][CH2:34]4)=[O:32])[N:27]3[CH3:30])=[CH:23][CH:22]=2)=[CH:18][CH:19]=1)(=[O:12])=[O:11].[H-].[Na+].I[CH3:55].O>CN(C=O)C>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[S:10]([N:13]([CH3:55])[C:14]1[CH:15]=[N:16][C:17]([O:20][C:21]2[CH:29]=[C:28]3[C:24]([CH:25]=[C:26]([C:31]([N:33]4[CH2:34][CH2:35][N:36]([CH2:39][C:40]5[CH:41]=[CH:42][C:43]([O:46][CH2:47][C:48]([F:50])([F:49])[F:51])=[CH:44][CH:45]=5)[CH2:37][CH2:38]4)=[O:32])[N:27]3[CH3:30])=[CH:23][CH:22]=2)=[CH:18][CH:19]=1)(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68496065HCID 68496065, compound

Product 1

HCID 68494659HCID 68494659, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4,6-trimethyl-N-[6-(1-methyl-2-{4-[4-(2,2,2-trifluoroethoxy)benzyl]piperazine-1-carbonyl}-1H-indol-6-yloxy)pyridin-3-yl]benzenesulfonamide (0.38 g, 0.53 mmol) in DMF (4 mL) was added 60% sodium hydride in oil (0.025 g, 0.63 mmol) under ice cooling and stirred for 10 minutes. Then to the mixture was added iodomethane (0.036 mL, 0.58 mmol) at 0° C. and the mixture was stirred for 2 hours. Water (8 ml) was added to the reaction mixture and extracted with AcOEt, the organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel column chromatography (AcOEt to AcOEt:MeOH=95:5) to give 0.28 g of the title compound as a colorless amorphous powder.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. extractionextracted with AcOEt
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (AcOEt to AcOEt:MeOH=95:5)

Sources & evidence

ORD record
ord-91a8ce23fc884d9b8a3ce63959d676ad
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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