Methyl iodide → HCID 18727259, compound

HRID 843013Notes

Reaction equation

HRID 843013 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 0.1M 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 0.1M 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-68625d46d38c452cb785e6be94fa9822
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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