Hydrochloric Acid → HCID 86602798, compound

HRID 1444068Notes

Reaction equation

HRID 1444068 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].[OH:31][CH2:32][C@@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1C(OC(C)(C)C)=O.[H-].[Na+].Cl>CN1CCCC1=O>[ClH:1].[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]([O:31][CH2:32][C@H:33]2[CH2:37][CH2:36][CH2:35][NH:34]2)=[C:23]([Cl:30])[N:22]=1)(=[O:10])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 643448(S)-(-)-N-Boc-prolinolHCID 11180148HCID 11180148, compound

Product 1

HCID 86602798HCID 86602798, compoundYield 145.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Procedure as for Example 115 using 2,3-dichloro-N-(5,6-dichloro-3-methoxy-2-pyrazinyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulphonamide (Example 66a) (0.29 g), tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (0.15 g) and sodium hydride (0.04 g of a 60% dispersion in oil) in N-methylpyrrolidinone (20 mL). The adduct was deprotected with HCl (4M in dioxane) to afford the titled adduct (0.2 g) as a white solid.

Sources & evidence

ORD record
ord-7bd488db4499493ab951e44b0535b4be
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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