Butylate → (RS)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one

HRID 1929497Notes

Reaction equation

HRID 1929497 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([C:8]([NH:12][C:13](=[O:16])[CH2:14]Cl)([CH3:11])[CH2:9][OH:10])[CH:7]=1.[K].CCSC([N:24]([CH2:29][CH:30]([CH3:32])[CH3:31])CC(C)C)=O>[Pd]>[C:29](=[N:24][C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([C:8]2([CH3:11])[NH:12][C:13](=[O:16])[CH2:14][O:10][CH2:9]2)[CH:7]=1)([C:30]1[CH:31]=[CH:11][CH:8]=[CH:9][CH:32]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 16181ButylateHCID 5462222PotassiumHCID 58155286(RS)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide

Product 1

HCID 58155288(RS)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a reaction sequence analogous to that described for the preparation of the optically active Building block H, the cyclization of the (RS)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide with potassium tent-butylate, followed by the palladium-catalyzed amination yielded the (RS)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one. Its reaction with Lawesson's reagent and the following treatment with hydrochloric acid yielded the title compound as a light yellow solid. Mass (calculated) C11H13FN2OS.ClH [276.762]; (found) [M+H]+=241.

Workup

  1. customIn a reaction sequence analogous to that described for the preparation of the optically active Building block H

Sources & evidence

ORD record
ord-0b300fcea7184af9ae3daa28fa8d6595
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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