Methyl iodide → HCID 59577945, compound

HRID 2194143Notes

Reaction equation

HRID 2194143 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:35][CH2:34][C:16]2([C:20](=[O:21])[N:19]([C:22]3[CH:33]=[CH:32][C:25]([C:26]([NH:28][CH:29]([CH3:31])[CH3:30])=[O:27])=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[CH2:15][CH2:14]1)(=[O:12])=[O:11].[CH3:36]I>C1COCC1.Cl>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]1[CH2:35][CH2:34][C:16]2([C:20](=[O:21])[N:19]([C:22]3[CH:23]=[CH:24][C:25]([C:26]([N:28]([CH:29]([CH3:31])[CH3:30])[CH3:36])=[O:27])=[CH:32][CH:33]=3)[CH2:18][CH2:17]2)[CH2:15][CH2:14]1)(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59577874HCID 59577874, compound2×

Product 1

HCID 59577945HCID 59577945, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To NaH (0.04 g, 55% suspension in oil, washed with pentane) was added at RT and under an argon atmosphere and at RT 4-[8-(2-chloro-benzenesulfonyl)-1-oxo-2,8-diaza-spiro[4.5]dec-2-yl]-N-isopropyl-benzamide (0.04 g), product of example 160), in THF (4 ml). The reaction mixture was stirred 1 hour at RT, then MeI (0.232 g) was added and stirring was continued overnight at RT until the conversion was complete. The reaction mixture was made acidic with 1M HCl (one drop) and stirred for one minute. The solvent was removed in vacuo, the residue adsorbed on silica gel and chromtographed over silica gel (eluent: AcoEt/CH2Cl2, gradient from 0 to 30%) to give the desired product as off-white solid. MS (ESI): 504.1 MH+).

Workup

  1. stirringstirring
  2. waitwas continued overnight at RT until the conversion
  3. stirringstirred for one minute
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-44b939c539ab4c73be5e98068f6216d1
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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