Triethylamine → HCID 10194939, compound

HRID 1444000Notes

Reaction equation

HRID 1444000 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]([C:21]1[C:26]([O:27][CH3:28])=[N:25][C:24](Cl)=[C:23]([Cl:30])[N:22]=1)COCC[Si](C)(C)C)(=[O:11])=[O:10].Cl.[NH:32]1[CH2:35][CH:34]([OH:36])[CH2:33]1.C(N([CH2:42][CH3:43])CC)C>C(#N)C.O>[C:34]([O:36][CH2:42][CH3:43])(=[O:10])[CH3:35].[CH3:4][CH2:5][CH2:6][CH:7]([CH3:2])[CH3:33].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:21]1[C:26]([O:27][CH3:28])=[N:25][C:24]([N:32]2[CH2:35][CH:34]([OH:36])[CH2:33]2)=[C:23]([Cl:30])[N:22]=1)(=[O:10])=[O:11]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 11180148HCID 11180148, compound

Product 2

HCID 10194939HCID 10194939, compoundHCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2,3-Dichloro-N-(5,6-dichloro-3-methoxy-2-pyrazinyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulphonamide (Example 66 part a) (0.20 g), azetidin-3-ol hydrochloride (0.082 g) and triethylamine (0.25 mL) in acetonitrile (3 mL) and water (0.5 mL) was stirred at room temperature. After 2 h, the mixture was evaporated and triturated with diethyl ether. The ethereal solution was evaporated and the residue dissolved in a 1 molar solution of tetrabutylammonium fluoride in THF (6 mL). After 16 h, the reaction mixture was concentrated and chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound as a white solid (0.024 g).

Workup

  1. customthe mixture was evaporated
  2. customtriturated with diethyl ether
  3. customThe ethereal solution was evaporated
  4. dissolutionthe residue dissolved in a 1 molar solution of tetrabutylammonium fluoride in THF (6 mL)
  5. waitAfter 16 h
  6. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a9d8aec65a644f55a97abfb1b286dace
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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