Triethylamine → HCID 59168104, compound

HRID 1443993Notes

Reaction equation

HRID 1443993 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].[C:31]([NH:34][CH2:35][CH2:36][NH2:37])(=[O:33])[CH3:32].C(N(CC)CC)C>C(#N)C>[Cl:30][C:23]1[C:24]([NH:37][CH2:36][CH2:35][NH:34][C:31](=[O:33])[CH3:32])=[N:25][C:26]([O:27][CH3:28])=[C:21]([NH:12][S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])(=[O:10])=[O:11])[N:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66082N-(2-aminoethyl)acetamideHCID 11180148HCID 11180148, compound

Product 1

HCID 59168104HCID 59168104, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,3-Dichloro-N-(5,6-dichloro-3-methoxy-2-pyrazinyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulphonamide (Example 66 part a) (0.26 g) was dissolved in acetonitrile (1.0 mL) and N-acetylethylenediamine (0.055 mL) and triethylamine (0.19 mL) added. After 48 h, the reaction mixture was concentrated and chromatography on silica gel eluting with ethyl acetate gave the title compound protected with the SEM group, as an oil (0.13 g). The oil was dissolved in dichloromethane (2.0 mL) and boron trifluoride etherate (0.14ml) added. After 2 h, ethyl acetate (20 mL) was added and the mixture washed with 5% aqueous citric acid (5 mL), dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate gave the title compound as a solid (0.031 g).

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-4b31a4d70eaf4ceb8e077bc7b4d4c50a
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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