Methyl iodide → HCID 18727259, compound

HRID 1856885Notes

Reaction equation

HRID 1856885 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[CH2:9]([O:16][NH:17][C:18]([C@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]1[S:26]([N:29]1[CH2:34][CH2:33][CH:32]([C:35]2[C:43]3[C:38](=[CH:39][CH:40]=[C:41]([F:44])[CH:42]=3)[NH:37][CH:36]=2)[CH2:31][CH2:30]1)(=[O:28])=[O:27])=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:9]([O:16][N:17]([CH3:1])[C:18]([C@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]1[S:26]([N:29]1[CH2:34][CH2:33][CH:32]([C:35]2[C:43]3[C:38](=[CH:39][CH:40]=[C:41]([F:44])[CH:42]=3)[NH:37][CH:36]=2)[CH2:31][CH2:30]1)(=[O:28])=[O:27])=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18727256HCID 18727256, compound

Product 1

HCID 18727259HCID 18727259, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Anhydrous potassium carbonate (736 mg, 5.33 mmol) and iodomethane (0.133 ml, 2.13 mmol) were added to a solution of N-benzyloxy-1-[4-(5-fluoroindol-3-yl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide (549 mg, 1.07 mmol) [prepared as described in Step 3 above] in dimethylformamide (11 ml) at RT. After 2 h, the reaction mixture was diluted with ethyl acetate (50 ml) and then washed with 0.1 M HCl, brine and dried over MgSO4. The solvent was removed in vacuo and the residue was chromatographed (PTLC, SiO2, 40% ethyl acetate/hexanes) to give N-benzyloxy-N-methyl-1-[4-(5-fluoroindol-3-yl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide (71%) as a white solid.

Workup

  1. washwashed with 0.1 M HCl, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customthe residue was chromatographed (PTLC, SiO2, 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-693bf0fa0ef44dafbf74700e4ee0f718
Source dataset
uspto-grants-2000_11
Patent number
US06143744

Reaction notes

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