Triethylamine → HCID 66817419, compound

HRID 1755138Notes

Reaction equation

HRID 1755138 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[CH2:11][CH2:12][S:13]([N:16]1[CH2:32][CH2:31][C:19]2([N:23]=[C:22]([CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH2:29])[NH:21][C:20]2=[O:30])[CH2:18][CH2:17]1)(=[O:15])=[O:14].[C:33](Cl)(=[O:43])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[Cl-].[NH4+]>C(Cl)Cl.O.CN(C=O)C>[CH2:24]([C:22]1[NH:21][C:20](=[O:30])[C:19]2([CH2:18][CH2:17][N:16]([S:13]([CH2:12][CH2:11][C:3]3[C:4]([CH3:10])=[CH:5][C:6]([N:8]([CH3:9])[C:33](=[O:43])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])=[CH:7][C:2]=3[CH3:1])(=[O:15])=[O:14])[CH2:32][CH2:31]2)[N:23]=1)[CH2:25][CH2:26][CH2:27][CH:28]=[CH2:29]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 11084623HCID 11084623, compoundHCID 66818016HCID 66818016, compound

Product 1

HCID 66817419HCID 66817419, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

The resulting crude product 8-[2-(2,6-dimethyl-4-methylamino-phenyl)-ethanesulfonyl]-2-hex-5-enyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (160 mg, 0.35 mmol) was dissolved in methylene chloride. 9-Decenoyl chloride (0.35 mmol) (prepared by allowing oxalyl chloride and a catalytic amount of DMF to act on 9-decenoic acid in methylene chloride) and triethylamine (0.195 ml, 1.4 mmol) were added, and the mixture was stirred at room temperature for 17 hours. A saturated aqueous ammonium chloride solution and water were added to the reaction solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give dec-9-enoic acid {4-[2-(2-hex-5-enyl-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl)-ethyl]-3,5-dimethyl-phenyl}-methyl-amide (Compound 1443) (100 mg, 48% in two steps).

Workup

  1. additionwere added
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aed67869e9e44b47867e8d36089bb93a
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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