Triethylamine → HCID 66817239, compound

HRID 1755092Notes

Reaction equation

HRID 1755092 reaction equation
[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C.[CH:17]1([C:23]2[NH:27][C:26](=[O:28])[C:25]3([CH2:33][CH2:32][N:31]([S:34]([CH2:37][C:38](=O)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[CH3:45])(=[O:36])=[O:35])[CH2:30][CH2:29]3)[N:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[OH-].[Na+]>C(Cl)Cl>[CH:17]1([C:23]2[NH:27][C:26](=[O:28])[C:25]3([CH2:33][CH2:32][N:31]([S:34]([C:37]#[C:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[CH3:45])(=[O:36])=[O:35])[CH2:30][CH2:29]3)[N:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 14798Sodium HydroxideHCID 1670692-Chloro-1-methylpyridinium iodide2×HCID 66817150HCID 66817150, compound

Product 1

HCID 66817239HCID 66817239, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-1-methyl-pyridinium iodide (18 mg, 0.070 mmol) and triethylamine (0.28 mL, 1.98 mmol) were added to a solution of 2-cyclohexyl-8-(2-oxo-2-o-tolyl-ethanesulfonyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (20 mg, 0.046 mmol) in methylene chloride (1.0 mL), and the mixture was stirred at room temperature for 19 hours. 2-Chloro-1-methylpyridinium iodide (18 mg, 0.070 mmol) and triethylamine (0.28 mL, 1.98 mmol) were further added, and the mixture was stirred at room temperature for five hours. A 1 M aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was stirred at room temperature for 20 minutes. The aqueous layer was extracted with methylene chloride, and the organic layer was washed with a 1 M aqueous sodium hydroxide solution, water and saturated brine and dried over sodium sulfate. The organic layer was concentrated, and the residue was then silica gel column chromatography to give 2-cyclohexyl-8-(2-o-tolyl-ethynesulfonyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (15 mg, 79%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for five hours
  2. stirringthe mixture was stirred at room temperature for 20 minutes
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. washthe organic layer was washed with a 1 M aqueous sodium hydroxide solution, water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-0efc8b6187af477f92d14a548ad37ef7
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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