HCID 18629437, compound → Ammonium Hydroxide

HRID 1060897Notes

Reaction equation

HRID 1060897 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:17][S:18]([CH2:20][CH:21]([CH2:23]C)[CH3:22])=[O:19])([C:11]2[N:12]([CH3:16])[CH:13]=[N:14][CH:15]=2)C)=[CH:5][C:4]=1[F:25])#[N:2].[F:26][C:27]1[CH:32]=[CH:31]C([Mg]Br)=[CH:29][CH:28]=1>C1COCC1.CCOCC.C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[N:12]([C:16]3[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=3)[CH:13]=[N:14][CH:15]=2)=[N:17][S:18]([CH2:20][CH:21]([CH3:22])[CH3:23])=[O:19])=[CH:5][C:4]=1[F:25])#[N:2].[NH4+:2].[OH-:19]

Participants

8

Reactant 2

HCID 18629437HCID 18629437, compoundHCID 178418676HCID 178418676, compound

Product 2

HCID 14923Ammonium HydroxideHCID 86758855HCID 86758855, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-[1-(4-cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2 ethylpropanesulfinamide (Example 1, Step I) (2.0 g, 6.02 mmol) in THF (20 mL) at 0° C. in an ice-H2O bath was added 4-fluorophenyl magnesium bromide (7 mL of a 2M solution in Et2O) over a 1 h period. Grignard reagent was added until the reaction mixture color remained dark brown/black. After 2 h the reaction mixture was diluted with CH2Cl2 and aqueous saturated NaHCO3 solution, layers separated, the aqueous layer washed with CH2Cl2 (2×), the organics combined, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound after chromatography (SiO2, 1-5 MeOH/CH2Cl2 with NH4OH). MS(M+1) 428.

Workup

  1. customseparated
  2. washthe aqueous layer washed with CH2Cl2 (2×)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-999b0b7370934ff9a1593c9701a825eb
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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